Chemistry M11

Laboratory Manual

Laboratory Experiments for General,

Organic, and Biochemistry

Compiled by the Department of

Chemistry at Moorpark College

Version 2.0

Fall 2020 – Present

NH2
O
O
CN
NH2
N N
Co The Vitamin B12 molecule shown is useful in the treatment of
N N
H2N pernicious anemia and other diseases. Enzymes derived from
O
O vitamin B12 accelerate a large range of important reactions
NH2 including those involved in producing red blood cells.
HN N
O
HO
N
O O
P
O O
O
CH2OH
 Moorpark College Department of Chemistry
Chemistry 11 Lab Manual Table of Contents

Laboratory Experiments Page Number

Experiment 1 – Separation of Copper(II) Sulfate from Sand ............................................. 3
Experiment 2 – Measurements............................................................................................ 6
Experiment 3 – Properties of Solutions ............................................................................ 13
Experiment 4 – Double Displacement Reactions ............................................................. 20
Experiment 5 – Single Displacement Reactions ............................................................... 25
Experiment 6 – Precipitation of Strontium Sulfate ........................................................... 29
Experiment 7 – Ionization and the Nature of Acids, Bases, and Salts.............................. 33
Experiment 8 – Acid/Base Titrations ................................................................................ 42
Experiment 9 – Structure in Inorganic & Organic Compounds ....................................... 48
Experiment 10 – Stereochemistry & Use of Molecular Models ....................................... 57
Experiment 11 – Paper Chromatography.......................................................................... 63
Experiment 11 – Identification of Hydrocarbons ............................................................. 67
Experiment 13 – Properties of Amines and Amides ......................................................... 75
Experiment 14 – Synthesis & Characterization of Acetylsalicylic Acid .......................... 80
Experiment 15 – Carbohydrates........................................................................................ 84
Experiment 16 – Analysis of Lipids ................................................................................. 90
Experiment 17 – Viscosity & Secondary Structure of DNA ............................................ 94
Experiment 18 – Spectrophotometric Analysis of Blood Glucose ................................. 101
Experiment 19 – Synthesis and Characterization of Soap .............................................. 106
Experiment 20 – DNA Extraction from an Onion .......................................................... 111

Appendix Page Number

Solubility Rules ............................................................................................................... 116
Names, Formulas, and Charges of Common Polyatomic Ions ....................................... 117
Moorpark College Chemistry Department Laboratory Report Rubric ........................... 118
Periodic Table of the Elements ....................................................................................... 120

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Experiment 1 – Separation of Copper(II) Sulfate from Sand

Discussion

Mixtures are a combination of substances in which the components keep their individual
characteristics. Mixtures have variable proportions and can be separated by simple physical
means. The mixture’s components have different physical properties like melting point, boiling
point, or solubility that allow us to selectively remove individual components from the mixture.
Once separated, the percentage of each component in the original mixture can be calculated.

In this experiment, you will separate a mixture of copper(II) sulfate and sand using the physical
property of solubility. You will learn about certain methods of separation that include
decantation, filtration, and evaporation. Finally, the Law of Conservation of Mass will be
applied to check the validity of your final calculations.

Procedure

1. Weigh about 4 –5 grams of the CuSO4/sand mixture in a 100 mL beaker on the laboratory
balance by taring (your instructor will explain and demonstrate).

2. Add 10-15 mL of D.I. water to the beaker, and swirl. Next, weigh and record the weight of
a piece of filter paper AND an evaporating dish separately. Then assemble the filter
apparatus as demonstrated by the instructor, filter the mixture, and collect the filtrate
(liquid) onto the evaporating dish. Use your wash bottle (filled with D.I. water) to transfer
all the undissolved solid from the beaker to the filter paper. After all the liquid has drained
through the filter, wash the filter with small portions of D.I. water from the wash bottle
until the washings are colorless. Again, make sure you collect ALL the filtrate and
washings in the evaporating dish. Try to use small amounts of water. You will be
evaporating the liquid; the more water you add, the longer it will take!

3. Prepare a steam bath by placing a 250 mL beaker, 2/3 full of water with 4 – 5 boiling chips,
on a wire screen on a ring stand. Place the evaporating dish carefully on the beaker and
heat the water to boiling. Heat the steam bath until the filtrate has completely evaporated.
Do NOT let the steam bath boil to dryness; you may have to refill the water in the beaker
occasionally. If the beaker goes dry, it must be cooled before adding water to prevent the
beaker from cracking!

4. Open the filter paper onto a large watch glass. Dry the solid on the filter paper in the drying
oven for 20 minutes.

5. Once your equipment has cooled, weigh both the evaporating dish and filter paper
separately. Compute the weight of the CuSO4 sample and sand by difference. Calculate the
weight percent CuSO4 and sand in the sample.

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Data and Calculations for Experiment 1

Mass of CuSO4/sand mixture _______________

Mass of empty evaporating dish _______________

Mass of evaporating dish and dry CuSO4 _______________

Mass of CuSO4 _______________

Mass of empty filter paper _______________

Mass of filter paper and sand _______________

Mass of sand _______________

Total mass of products _______________

Calculated total percent yield _______________

Percent by mass of CuSO4:

Show Calculation _______________

Percent by mass of sand:

Show Calculation _______________

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Questions

1. Many students do NOT recover 100% of the original mixture. Describe at least TWO
possible problems that could cause LESS than 100% recovery of the mixture.

2. A student obtained the following data:

Mass of beaker 25.87 g

Mass of beaker with mixture sample 28.12 g
Mass of evaporating dish 146.36 g
Mass of evaporating dish with dried salt 147.10 g
Mass of beaker with dried sand ???

However, this student spills her sand sample out of the evaporating dish before weighing
it. If the student believes in the Law of Conservation of Mass, what should have been the
weight of the beaker with the dried sand in it? Show all your work.

3. A student receives a sample of a mixture with three components: (1) solid iodine that is
first removed from the mixture by evaporation, (2) solid salt that is dissolved to separate it
from the third component, and (3) solid sand. The salt and sand are dried and weighed, but
the iodine escapes as a gas and is not recovered. The student starts with 4.25 g of the
mixture and recovers 1.16 g of salt and 2.40 g of sand. What is the percent of each
component in the original mixture? Show all your work.

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Experiment 2 – Measurements

Discussion

Experimental sciences, such as Chemistry, depend on making and using measurements

properly. The SI system of units (sometimes called the metric system) is used almost
exclusively. This system is very similar to our monetary system: $1 = 10 dimes = 100 cents =
1000 mils. In chemistry, the basic units of length, mass, and volume are the meter, gram, and
liter, respectively. They all are divided the same way. For example, 1 meter = 10 decimeters =
100 centimeters = 1000 millimeters. The kilo is also commonly used; it equals 1000 of the
basic unit. For example, 1 kilogram = 1000 grams.

Often you will be asked to compare your experimental or calculated value to an “accepted” or
theoretical value. The closer you are to the accepted value, the greater the accuracy of your
experiment. Percent error is a common method used for calculating accuracy: % error = 100 x
difference/accepted value. The accepted value could be located in a reference such as the
Handbook of Chemistry and Physics. The difference between your value and the accepted
value is then divided by the accepted value and multiplied by 100 to calculate the percent error.
The smaller the percent error, the more accurate your experimental value.

In science, an experimenter is allowed to estimate one more digit past what can be measured
exactly on an instrument. For example, if the smallest lines on a ruler are centimeters, and an
object’s length falls between 2 lines, more precision is gained by estimating between the lines.
Therefore, the length of an object might be reported as 25.5 cm. The reported numbers are
called “significant figures”, and the more precise the instrument, the more significant figures
it can produce.

A calculation cannot be any more precise than the least precise measurement. For example,
density is calculated by dividing the mass of an object by its volume. Therefore, the density of
an object might be 23.57 g / 4.2 mL = 5.61190476 g / mL. But, the least precise measurement
(the volume) only has a precision of 2 significant figures. Therefore, the density must be
reported as 5.6 g / mL.

Procedure

Record your data on the report form as you complete the measurements.4

A. Temperature

5 beakers with thermometers have been set up for you: (1) room temperature water,
(2) boiling water, (3) a mixture of ice and water, (4) a stirred mixture of ice and water, and
(5) a stirred mixture of ice, water and salt. Observe and record all temperatures to the
nearest 0.1 oC.

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B. Mass

When using any measuring device, never round off your raw data. If the balance fluctuates
on the last digit, estimate that value. Weigh a (1) 100-mL beaker, (2) a 250-mL Erlenmeyer
flask, (3) a plastic empty weighing boat, and (4) and then add approximately 2 grams of
sodium chloride to the weighing boat. Calculate the mass of the sodium chloride added.

C. Length

Using a metric ruler, measure the following in centimeters, remembering to estimate one
extra digit: (1) the length of the double arrow on the report sheet, (2) the length of the
external height of a 250-mL beaker, and (3) the length of a medium sized test tube.

D. Volume

The graduated cylinder is the most accurate equipment in your locker for measuring
volume and can give a precision of 0.1 mL. Water is attracted to the glass sides of the
cylinder, causing a curved effect called the meniscus. The cylinder should be read at eye
level using the bottom of the meniscus. In theory, a 250-mL Erlenmeyer flask with a
marking for 200 mL should have a volume of 200 mL at that mark! However the problem
is that volumes marked on beakers and flasks are only approximate values. Therefore, fill
a 250-mL Erlenmeyer flask to the 200 mL mark with water, transfer this volume of water
to a 250-mL graduated cylinder, and determine the exact volume.

It is often convenient to estimate volumes of 5 and 10 mL simply by observing the height

of a liquid in a test tube. Use your graduated cylinder to place 5 and 10 mL of water in a
medium-sized test tube and measure the heights in cm.

E. Density

Density measures the “compactness” of material. For example, lead has a high density, and
Styrofoam has a low density. Mathematically, this compactness is expressed as mass per
unit volume. In chemistry, we use grams and milliliters: D = g/mL. Density is an intrinsic
value; it does not depend on the amount of sample taken. We will take advantage of this
by measuring the density of various sample sizes and averaging their densities:

1. Obtain 5 pieces of the same object and record its name on the data sheet.

2. Keep track of the 5 objects by placing them in numbered test tubes.

3. Weigh each object and record the values on the data sheet.

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4. Choose the appropriate size graduated cylinder (smallest size that will hold the object
plus enough water). Add enough water to the graduated cylinder to be able to cover
your largest sample. Record the volume to the highest precision (0.1 mL or better).

5. Carefully add the sample to the graduated cylinder. There are two things to watch out
for: breaking the cylinder and splashing water out. Tilting the cylinder and gently
sliding the object in minimize both of these risks. Record the new volume.

6. Repeat with each sample piece. If the sample pieces are small, the pieces can remain in
the graduated cylinder until all sample pieces have been added to the cylinder.

7. Determine the density of each piece and the average density.

8. Graph the cumulative data. Use the largest values of mass and volume to determine
your x and y scales. Choose the scale to use most of the available graph. Place a data
point at the origin (0.00 grams and 0.00 mL), then place all your other cumulative data
points.

9. Using a straight edge, draw the best-fit line through the data points (through the center
of the points, include the origin on the line).

10. Choose a point on the line near the high end of the line that passes through the graph’s
cross hairs. The slope is the mass of this point divided by its volume. The slope of this
graph is another way of determining the average density of the data points.

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Data and Calculations for Experiment 2

Measurements

A. Temperature
1. Water at room temperature _______________ °C

2. Boiling point _______________ °C

3. Ice water
Unstirred _______________ °C

Stirred _______________ °C

4. Ice water with salt added _______________ °C

B. Mass
1. 100 mL beaker ________________ g

2. 250 mL Erlenmeyer flask ________________ g

3. Weighing boat ________________ g

4. Mass of weighing boat + sodium chloride ________________ g

Mass of sodium chloride (show calculation setup) ________________ g

C. Length

1. Length of _______________ cm

2. Height of 250 mL beaker _______________ cm

3. Length of test tube _______________ cm

D. Volume

1. 200 mL mark (from Erlenmeyer flask) water

transfered to graduated cylinder ______________ mL

2. Height of 5.0 mL of water in test tube ______________ cm

3. Height of 10.0 mL of water in test tube ______________ cm

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 E. Data Sheet for Density of an Object

Name of Object _______________________

Graph the following:

Sample Object Initial mL Volume Density Cumulative Cumulative Cumulative
# Mass mL H2O object (g/mL) Sample #s volume object

Chemistry M11 Laboratory Manual

(g) H2 O w/ (mL) (mL) mass (g)
Object (x-axis) (y-axis)

1 _______ _______ _______ _______ _________ 1 ___________ ___________

Name: _________________________________

2 _______ _______ _______ _______ _________ 1+2 ___________ ___________

3 _______ _______ _______ _______ _________ 1+2+3 ___________ ___________

4 _______ _______ _______ _______ _________ 1+2+3+4 ___________ ___________

5 _______ _______ _______ _______ _________ 1+2+3+4+5 ___________ ___________

Average Density = _________

Page 10
Section: _____________________
Name: _________________________________ Section: _____________________

Graph of Cumulative Mass versus Cumulative Volume

Average density of sample from calculated data: _________________________

Average density from graph: _________________________

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Questions

1. Which would work better in this experiment as an unknown solid whose density is to be
determined, wood chips or small quartz rocks? Explain your choice.

2. Why is it best to use a smaller graduated cylinder as opposed to a larger graduated

cylinder for this experiment?

3. How well does the average density from the table and density from the slope of the graph
compare? Which value is closer to the accepted density of your metal? (Refer to the
Handbook of Chemistry and Physics). Calculate the percent error between your better
value and the handbook value.

4. What is the density of a 9.343 gram piece of metal that causes the level of water in a
graduated cylinder to rise from 5.1 to 8.1 mL when the metal is emerged in the water?
Consider significant figures when doing the calculation.

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Name: _________________________________ Section: _____________________

Experiment 3 – Properties of Solutions

Discussion

In today’s lab, you will investigate the qualitative nature of solutions. The first step is learning
some common terms.

Solute refers to a compound that dissolves in a solvent to form a solution. A solution can have
one or more solutes, but only one solvent. The solvent is the compound that is predominant in
the solution. A solute is said to be dissolved when it forms a clear, but not necessarily colorless,
liquid. Thus, sugar dissolves in water, but fine sand and dust form suspensions which are not
true solutions.

Solvents can be sorted by their polarity. Water is very polar, while benzene, decane, and
gasoline are considered non-polar. The term organic solvent refers to most solvents other than
water that are carbon-containing. Organic solvents can be either polar or non-polar, depending
upon their structure. For example, methanol and ethanol are polar organic solvents, while ether
and acetone are less polar, and decane and benzene are considered non-polar organic solvents.

Solubility is a measure of how much of a compound can eventually dissolve in a solvent. If a

solid does not dissolve, the compound is said to be insoluble. It can also be described as
slightly soluble, moderately soluble, or very soluble. If the compound is a liquid (not a solid)
it can dissolve and is described as miscible, or instead forms two layers and is called
immiscible. Ethanol and water are miscible, while oil and water are immiscible.

Concentration refers to the amount of solute relative to the total volume of solution. A dilute
solution has little solute per 100 grams of solution, while a concentrated solution has more
solute. A solution is considered saturated when no more solute can dissolve in that solution
without it precipitating thereafter.

A supersaturated solution is a solution that holds more solute than it normally can hold at that
temperature. Given time, some solute will precipitate out of solution. In other words, the
solution is unstable over time.

Concentration can be measured using several terms. “Proof” is used to measure alcohol content
in liquor and beer. Chemists tend to use mass percent and molarity, which are defined below.
Remember that mass percentages range from 0 to 100%, and molarities are generally less than
18 M.* Very few compounds can form solutions with higher concentrations.

mass of X
Mass percent of X = × 100 %
mass of X + mass of solvent

moles of X
Molarity of X =
Liters of total solution

*
“M” represents “molar,” the unit used to measure molarity. It is equal to mol / L.

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Procedure

A. Concentration of a Saturated Solution.

In this section, you’ll figure out how many grams of potassium chloride per mL of solution
were present in a pre-made saturated solution of KCl.

1. Weigh a clean, dry evaporating dish. In this dish, add 6.0 mL of solution and place the
dish in a 250-mL beaker of boiling water. Evaporate the solution until a white solid is
present in the dish. Don’t let the boiling water bath go dry. This step will take
approximately half an hour.

2. Remove the dish from the boiling water with tongs. Place the dish on a wire mesh and
gently heat with a Bunsen burner. If you heat too strongly, the solid may “pop” and you
will lose some.

3. Let the dish cool until it can be touched safely. Weigh the flask to find out how many
grams of potassium chloride are present.

Cleanup: Wash the solid down the drain.

B. Relative Solubility of a Solute

In this section, you will determine whether iodine, a reddish solid, dissolves better in water
or decane.

1. Take a test tube and add about 5 mL of water and 2 mL of decane. Stopper the test tube
and give it a gentle shake. Note which layer was on top.

2. To this tube, add 5 mL of saturated iodine-water solution. Gently shake again and see
which layer has more color.

Cleanup: Empty the test tube into the waste labeled “Decane Waste”.

C. Miscibility of Liquids

In this section, you will find out what liquids are miscible with water.

Take three dry test tubes and add the following pair of liquids. Stopper the test tubes and
gently shake them. Are there two layers or one?

1. 1 mL of kerosene and 1 mL of isopropyl alcohol

2. 1 mL of kerosene and 1 mL of water
3. 1 mL of isopropyl alcohol and 1 mL of water

Dispose of the first two kerosene mixtures in the “Kerosene Waste” container.

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D. Effect of Particle Size on Rate of Dissolution

Fill a test tube with about 0.5 cm of fine crystals of sodium chloride. Fill a second test tube
with about 0.5 cm of coarse crystals of sodium chloride. Add 10 mL of water to each tube
and shake both tubes an equal number of times. Shake both tubes equally. Time how long
it takes to dissolve each.

These solutions can be disposed of down the sink.

E. Effect of Temperature on Dissolution

1. Weigh out two 0.5 g samples of fine sodium chloride crystals. Take two 250-mL
beakers and add 50 mL of water to them. Heat one of the beakers to boiling, then let it
cool for one minute.

2. Add the salt samples to each beaker and time how long it takes to dissolve each.

3. As soon as the salt dissolves, gently swirl the hot water and observe the denser salt
layer in the bottom of the flask. Repeat the process with the cold water.

These solutions can be disposed of down the sink.

F. Solubility versus Temperature; Saturated and Unsaturated Solutions

1. Weigh out 1.0 g of NaCl and 1.0 g of NH4Cl and place them in separate, labeled test
tubes and add 5 mL of water. Stopper the test tubes and shake the tubes until the salts
dissolve.

2. Add another 1.4 g of NaCl to the NaCl solution, and another 1.4 g of NH4Cl to the
NH4Cl solution. Stopper and shake the tubes for 3 minutes. Note whether or not the
salts dissolved.

3. Remove the stoppers and place both tubes in a beaker of boiling water, gently shaking
occasionally, and note the results after 5 minutes.

4. Remove the tubes and cool with running tap water for one minute and record your
observations. Let the solutions stand for a few minutes and record your observations.

Pour the solutions down the drain.

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G. Ionic Reactions in Solution

1. Place a small lump of pea-sized quantities of a) barium chloride, b) sodium sulfate, c)

sodium chloride, and d) barium sulfate into four separate labeled test tubes.

2. Add 5 mL of water, stopper the tubes, and shake them. Which sample(s) do(es) not
dissolve?

3. Mix the barium chloride and sodium sulfate together and note the results.

4. Write an equation that describes the results of these test tubes being mixed.

Dispose of all solutions in the “Barium waste” container.

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Data and Calculations for Experiment 3

A. Concentration of a Saturated Solution (record all masses as x.xxx g)

1. a) Mass of evaporating dish _______________

b) Mass of evap. dish and potassium chloride solution _______________

c) Mass of evap. dish and residue _______________

2. Calculate: (show setups)

a) Mass of potassium chloride solution _______________

b) Mass of residue _______________

c) Mass of water in potassium chloride solution

_______________

d) Mass percent of potassium chloride in the solution

_______________

e) Grams of potassium chloride per 100 g of water in the solution

_______________

B. Relative Solubility of a Solute in Two Solvents

1. a) Which liquid is denser, decane or water? _______________

b) How did you decide which layer was water?

2. What is the color of iodine in water? _______________

What is the color of iodine in decane? _______________

3. Which solvent dissolves more iodine? How did you decide this?

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Name: _________________________________ Section: _____________________

C. Miscibility of Liquids

1. Which liquids were miscible with each other?

2. Which liquids were immiscible with each other?

D. Particle Size and Dissolution Rates

1. How long did it take the fine salt crystals to dissolve?

2. How long did it take the coarse salt crystals to dissolve?

E. Temperature and Dissolution Rates

1. How long did it take the salt crystals to dissolve in hot water?

2. How long did it take the salt crystals to dissolve in cold water?

F. Temperature and Solubility

1. Was the solution with 1.0 g of NaCl in 5.0 mL water saturated at room temperature?

2. Was the solution with 1.0 g of NH4Cl in 5.0 mL water saturated at room temperature?

3. Was the solution with 2.4 g of NaCl in 5.0 mL water saturated at room temperature?

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4. Was the solution with 2.4 g of NH4Cl in 5.0 mL water saturated at room temperature?

5. Which salt was least soluble at higher temperatures?

6. At the higher temperatures, was the NaCl solution saturated?

7. At the higher temperatures, was the NH4Cl solution saturated?

8. What happened to the NaCl solution when it was cooled back to room temperature?

9. What happened to the NH4Cl solution when it was cooled back to room temperature?

G. Ionic Reactions in Solution

1. Write the formulas for the following:

barium sulfate _________

barium chloride _________

sodium sulfate _________

sodium chloride _________

2. Write the equation that shows the reaction of barium chloride and sodium sulfate. Use
state indicators such as (aq) and (s) for all compounds.

3. Which compound is the white precipitate? How do you know this?

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Name: _________________________________ Section: _____________________

Experiment 4 – Double Displacement Reactions

Discussion

In this experiment, double displacement reactions will be studied, where two water solutions,
each containing positive and negative ions, will be combined. Consider the generalized
reaction shown below:

AB + CD → AD + CB

where AB exists as A+ and B– ions in solution, and CD exists as C+ and D– ions in solution.
Each of the positive ions can combine with the negative ion of the other compound as shown
above. But the question then becomes: has there been a reaction? To answer this question, we
look at the products. Is either one an insoluble compound giving a precipitate (information
available from a solubility table), is either one a gas or producer of a gas, or would a
temperature change be predicted? Has a weak electrolyte such as a weak acid been formed? If
no to all of these, then no reaction occurs; this is simply a mixture. If yes to any one or more
of these, then a reaction occurs.

Procedure

Each part of the experiment below consists of mixing equal volumes of two solutions from
dropper bottles in a 24 well-plate. Place 5 drops of each indicated chemical in the well-plate.
Write your observations on the report sheet. Note the formation of any precipitate or gas. If
neither results, test the well-plate with a thermometer for any temperature change. If no change
is noted, write NR (No Reaction) for the mixture. Note: NH3(aq) = NH4OH(aq)

1. Mix 5 drops of 0.1 M NaCl(aq) with 5 drops of 0.1 M KNO3(aq).

2. Mix 5 drops of 0.1 M NaCl(aq) with 5 drops of 0.1 M AgNO3(aq).
3. Mix 5 drops of 10% NaOH(aq) with 5 drops of dilute 6 M HCl(aq).
4. Mix 5 drops of 0.1 M BaCl2(aq) with 5 drops of dilute 3 M H2SO4(aq).
5. Mix 5 drops of dil. 6 M NH3(aq) with 5 drops of dilute 3 M H2SO4(aq).
6. Mix 5 drops of 0.1 M CuSO4(aq) with 5 drops of 0.1 M Zn(NO3)2(aq).
7. Mix 5 drops of 0.1 M Na2CO3(aq) with 5 drops of 0.1 M CaCl2(aq).
8. Mix 5 drops of 0.1 M CuSO4(aq) with 5 drops of 0.1 M NH4Cl(aq).
9. Mix 5 drops of 10% NaOH(aq) with 5 drops of dilute 6 M HNO3(aq).

Dispose of all solutions in the appropriate WASTE CONTAINER in the hood.

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Data for Experiment 4

Record your observations for each combination below. If a reaction occurs, write balanced
MOLECULAR and NET-IONIC equations. If no reaction occurs, write NR. Make sure to
include the physical states of all the products.

1. NaCl(aq) and KNO3(aq)

Observations:

Molecular:

Net-Ionic:

2. NaCl(aq) and AgNO3(aq)

Observations:

Molecular:

Net-Ionic:

3. NaOH(aq) and HCl(aq)

Observations:

Molecular:

Net-Ionic:

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4. BaCl2(aq) and H2SO4(aq)

Observations:

Molecular:

Net-Ionic:

5. NH4OH(aq) and H2SO4(aq)

Observations:

Molecular:

Net-Ionic:

6. CuSO4(aq) and Zn(NO3)2(aq)

Observations:

Molecular:

Net-Ionic:

7. Na2CO3(aq) and CaCl2(aq)

Observations:

Molecular:

Net-Ionic:

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8. CuSO4(aq) and NH4Cl(aq)

Observations:

Molecular:

Net-Ionic:

9. NaOH(aq) and HNO3(aq)

Observations:

Molecular:

Net-Ionic:

Questions

1. For each of the reactions listed below, write balanced molecular and net-ionic equations.
If no reaction occurs, write NR. Assume all reactants are aqueous unless otherwise noted.
Include all physical states.

A. Lead(II) nitrate and magnesium sulfate solutions are combined.

Molecular:

Net-Ionic:

B. Zinc chloride solution is poured into a solution of ammonium carbonate.

Molecular:

Net-Ionic:

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C. Magnesium chloride solution is mixed with nickel(II) nitrate solution.

Molecular:

Net-Ionic:

D. Cobalt(II) sulfate and lithium sulfide solutions are combined.

Molecular:

Net-Ionic:

E. Sodium hydroxide solution is poured into a solution of cobalt(II) chloride.

Molecular:

Net-Ionic:

F. Solid zinc bromide is mixed with a solution of potassium phosphate.

Molecular:

Net-Ionic:

G. Solutions of ammonium sulfate and sodium chloride are combined.

Molecular:

Net-Ionic:

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Experiment 5 – Single Displacement Reactions

Discussion

The chemical reactivity of an element is related to its tendency to lose or gain electrons. In
theory, it is possible to arrange nearly all the elements into a single series in order of their
reactivities. A series of this kind indicates which free elements are capable of displacing other
elements from their compounds, known as the activity series. To illustrate the preparation of
such a list, we will examine certain single displacement reactions, symbolized generically
below:

A + BC → B + AC

where metal (A) comes into contact with a solution of a metal salt, acid, or water (BC). Metal
(B) and metal salt (AC) are formed if A is the more active metal. If metal B is more active than
element A, no reaction occurs.

Procedure

Obtain a 24 well-plate and place it on a sheet of white paper. Fill wells 1 to 6 with the following
solutions (each well should be approximately ½ full of solution).

Well 1: Silver nitrate, AgNO3

Well 2: Copper(II) nitrate, Cu(NO3)2
Well 3: Lead(II) nitrate, Pb(NO3)2
Well 4: Magnesium sulfate, MgSO4
Well 5: 3 M sulfuric acid, H2SO4
Well 6: 3 M sulfuric acid, H2SO4

Clean the metal pieces with fine sandpaper to expose fresh metal surfaces. Place copper in
well 1, lead in well 2, zinc in both wells 3 and 4, copper in well 5, and another piece of zinc in
well 6.

Observe the contents of each carefully and record any evidence of a chemical reaction. Some
of these reactions may be slow or no reaction may occur. Take your time.

Once the experiment is completed, remove the metal strips with your forceps and place them
in the appropriate waste boat located along the lab bench top. DO NOT allow the metal strips
to go into the sink. Then pour the solutions from the well plate into the appropriate waste
containers in the hood. DO NOT pour the solutions down the drain as they contain heavy
metals that can be toxic.

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Data for Experiment 5

Record your observations for each combination below. If a reaction occurs, write balanced
MOLECULAR and NET-IONIC equations. If no reaction occurs, write NR. Make sure to
include the physical states of all the products.

1. Cu(s) and AgNO3(aq)

Observations:

Molecular:

Net-Ionic:

2. Pb(s) and Cu(NO3)2(aq)

Observations:

Molecular:

Net-Ionic:

3. Zn(s) and Pb(NO3)2(aq)

Observations:

Molecular:

Net-Ionic:

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4. Zn(s) and MgSO4(aq)

Observations:

Molecular:

Net-Ionic:

5. Cu(s) and H2SO4(aq)

Observations:

Molecular:

Net-Ionic:

6. Zn(s) and H2SO4(aq)

Observations:

Molecular:

Net-Ionic:

Questions

1. Complete the following table by writing the symbols of the two elements whose reactivities
are being compared in each test:

Well # 1 2 3 4 5 6
Greater
Activity
Lesser
Activity

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2. Based upon the comparisons in the table, draw further conclusions by:

A. arranging Pb, Mg, and Zn in order of decreasing activity (most active first).

__________________ > __________________ > __________________

B. arranging Cu, Ag, and Zn in order of decreasing activity (most active first).

__________________ > __________________ > __________________

C. arranging Mg, H, and Ag in order of decreasing activity (most active first).

__________________ > __________________ > __________________

3. Now arrange the five metals from Question #2 above in order of decreasing activity.
Explain why the position of hydrogen (H2) cannot be exactly assigned.

___________ > ___________ > ___________ > ___________ > ___________

4. What additional test(s) would be required to determine the exact position of hydrogen in
the activity series of elements in this study?

5. Would silver react with dilute hydrochloric acid? Briefly explain why or why not.

6. Would magnesium react with dilute sulfuric acid? Briefly explain why or why not.

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Experiment 6 – Precipitation of Strontium Sulfate

In this experiment, you will study a precipitation reaction between sodium sulfate and
strontium chloride. You will collect, dry, and weigh the precipitate and compare this
experimental yield to the theoretical yield.

Procedure

Weigh a clean, dry, 100-mL beaker. Add about 0.25 g (0.350 g max!) of solid sodium sulfate
to the beaker and weigh it again. Dissolve the sodium sulfate in about 20 mL of D.I. water.
Add 5 mL of 0.5 M strontium chloride solution and heat for fifteen minutes. Try to keep the
mixture from boiling.

After the heating period has passed for the mixture, set it aside to return to room temperature,
and then cool it further by putting the beaker in a cold water bath. Your precipitate should
settle to the bottom, leaving a relatively clear solution above it. Obtain a piece of filter paper
and weigh it on the analytical balance.

Set up a vacuum filtration apparatus with a Büchner funnel and your weighed filter paper (your
instructor will show you how). Using a stirring rod to guide the stream of liquid, pour the
contents of the beaker into the Büchner funnel. Use your wash bottle (filled with D.I. water) to
rinse any solid out of the beaker and into the filter. Make sure no precipitate remains in the
beaker or on the stirring rod. Fill the beaker with 15 mL of D.I. water, swirl it around, and then
pour it into the filter. Repeat the washing process, and then draw air through the funnel for a
few minutes to help dry the crystals.

Turn off the vacuum, carefully remove the filter paper containing your precipitate with a
spatula, and place it over a watch glass. Fill a 100-mL beaker half-way with water, place the
watch glass with filter paper over the beaker, and heat to boil for twenty minutes to dry the
precipitate (alternatively, you can place the watch glass with filter paper in a drying oven at
130 °C for twenty minutes).

Allow to cool, then determine the mass of your precipitate. Heat for another five minutes, cool,
and reweigh. The two weights should agree within ±0.050 g or a third heating should be done.

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Data and Calculations for Experiment 6

1. Weight of empty beaker _____________________

2. Weight of beaker and sodium sulfate _____________________

3. Weight of sodium sulfate

Show Calculation _____________________

4. Moles of sodium sulfate

Show Calculation _____________________

5. Moles of strontium chloride

moles SrCl2 = (5 mL)(10–3/m)(0.5 M)

Show Calculation _____________________

6. Write a balanced MOLECULAR equation for the reaction:

7. Write a balanced NET-IONIC equation for the reaction:

8. Weight of empty filter paper _____________________

9. Weight of filter paper and dried precipitate (first time) _____________________

Weight of filter paper and dried precipitate (second time) _____________________

Weight of filter paper and dried precipitate (third time) _____________________

10. Weight of precipitate

Show Calculation _____________________

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11. Determine the theoretical yield (in grams) of strontium sulfate. What is your limiting
reactant and excess reactant?

Limiting Reactant: _____________________ Excess Reactant: _____________________

Show Calculation (theoretical product yield) _____________________

12. Determine the percentage yield of your reaction.

Show Calculation _____________________

13. What would have resulted from using half as much SrCl2(aq)?

Show Calculation _____________________

14. What would have resulted from using twice as much SrCl2(aq)?

Show Calculation _____________________

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15. Briefly describe how you could have improved your percentage yield in this experiment.

16. In your own words, write a cohesive, well-written summary of the background material
and underlying chemical principles pertinent to this experiment. If additional space is
needed, please use the back of this page. (For additional guidelines on writing this
introduction, please refer to the Moorpark College Chemistry Department Laboratory
Report Rubric found in the lab manual and department website.)

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Experiment 7 – Ionization and the Nature of Acids, Bases,

and Salts

Discussion

Compounds were defined by Sven Arrhenius to be acids if they release H+ ions in solution
when dissolved. This modern definition replaced older definitions based on taste (i.e acids tend
to be sour tasting) or if they changed litmus paper’s color. Bases (which tend to taste bitter)
were defined as compounds that give up OH– (hydroxide) ions in water. This definition was
limited to compounds in water and gives way to Brnsted-Lowry acid-base theory.

Brnsted-Lowry acid-base theory keeps the definition of an acid as something that donates an
H+ ion and defines bases as anything that accepts the H+ ion. Acids become proton donors;
bases become proton acceptors. In any acid-base equation, there will be one acid and one base
on each side of the equation. Which compound is an acid depends on whether that compound
is donating or accepting a proton.

NH3 + H2O → NH4+ + OH–

Base Acid Conj. Acid Conj. Base

HCl + H2O → Cl– + H3O+

Acid Base Conj. Base Conj. Acid

Water can function as both an acid and a base, depending on the other reagents!

HCl(aq) Hydrochloric acid H2SO4 Sulfuric acid

HBr(aq) Hydrobromic acid HC2H3O2 Acetic acid
HI(aq) Hydroiodic acid H2CO3 Carbonic acid
H3PO4 Phosphoric acid HNO3 Nitric acid

Many common strong bases contain hydroxides (OH–) and a metal.

NaOH Sodium hydroxide

KOH Potassium hydroxide
Ca(OH)2 Calcium hydroxide
Mg(OH)2 Magnesium hydroxide
NH4OH Ammonium hydroxide (best written as NH3.H2O)

Solutions that contain bases are called alkali or alkaline, from an Arabic word for “ashes”.
Campfire ashes (“bitter ashes”) contain hydroxides and carbonates of potassium and sodium,
which form basic or alkaline solutions. Compounds from plants that dissolve in water to form
alkaline solutions are called alkaloids. A common example of a bitter-tasting alkaloid is
caffeine.

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The term pH is used to measure the concentration of an acid in water. Thus, it is important to
remember that one acid can produce a range of pH values, depending upon the amount of acid
relative to the volume of solution. pH is defined by the equation pH = –log [H+]. Therefore, a
solution of 1.0 M HCl will produce 1.0 M H+ ions, assuming the HCl breaks up entirely. Since
log [1.0] = 0, the pH of this solution is 0. The pH of pure water will be 7.0, while the pH of a
very basic solution can be above 14.

pH < 7 acidic solutions pH = 7 neutral solution pH > 7 basic solution

When acids react with bases, the H+ from the acid and the OH– from the bases “cancel” each
other and form water molecules (“HOH”). The anions of the acid and the cations from the base
combine to form ionic compounds or salts. For example, consider the reaction of sulfuric acid
with sodium hydroxide:

H2SO4(aq) + 2NaOH(aq) → Na2SO4(aq) + 2H2O(l)

Reactions of Oxides with Water

The oxides of elements often react with water to form new compounds. Depending upon which
family the element is in, the new compound may be acidic or basic. For example, sulfur can
be oxidized to form sulfur trioxide, which reacts with water to make sulfuric acid. Consider
the following balanced equations:

S + O2 → SO2

2SO2 + O2 → 2SO3

SO3 + H2O → H2SO4

Carbon dioxide reacts with water to form carbonic acid as follows:

CO2 + H2O → H2CO3

The metal oxides react with water to form basic compounds. Calcium oxide reacts with water
to form calcium hydroxide, while magnesium oxide reacts with water to form magnesium
hydroxide:

CaO + H2O → Ca(OH)2

MgO + H2O → Mg(OH)2

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Electrolytes

Surprisingly, pure distilled water does not conduct electricity. In order for a charge to pass
through water, it needs to be carried by positive and negative charges. The more charges, the
more current can pass. If the charges cannot move, as in solid salts with no water present, then
electricity cannot be conducted.

Compounds can be divided into strong electrolytes, weak electrolytes, and non-electrolytes
depending upon how well they conduct electricity when dissolved in solution. Remember that
compounds that don’t dissolve in the solvent shouldn’t be called electrolytes at all. For
example, iron bars, wood, or plastics are not electrolytes regardless of whether they conduct
electricity or not.

In a strong electrolyte, the compound breaks up into cations or anions in a process called
“dissociation”. In a weak electrolyte, some of the compound dissociates into ions, even though
the entire compound dissolves. In non-electrolytes, the compound dissolves but does not break
up at all.

Procedure

A. Electrolytes

In this part of the experiment, your instructor will demonstrate the conductivity of various
solutions and reactions.

B. Investigating Acids

1. Reactions of Acids with Metals

a. Take four separate test tubes and place 5 mL of 6 M HCl in tube #1, 3 M H2SO4 in
tube #2, 6 M HNO3 in tube #3, and 6 M acetic acid in tube #4.

b. Put roughly a 2 cm strip of magnesium metal into each tube. Record the results.

c. As the metal is still bubbling, place a glowing piece of wood (splint) into the test
tube.

2. Measurement of pH and Acidity

a. Place 5 mL of water in a test tube and add 2 drops of a phenolphthalein indicator

solution in it. Add a few drops of dilute hydrochloric acid and record what happens.

b. There are three solutions of HCl prepared in front of the classroom. The most
concentrated, 0.1 M HCl, is one hundred times more concentrated than the weakest
solution, the 0.001 M HCl. Use the pH meter to record the pH’s of the three
solutions.

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3. Reactions of Acids with Carbonates and Bicarbonates

a. Take a 100 mL beaker and just cover the bottom with a thin layer of sodium
bicarbonate (baking soda). Add about 4 to 5 mL of diluted (6 M) HCl to the beaker.
Record the results. Lower a lit match into the beaker and record what happens.

b. Try the above reaction again with a chip of calcium carbonate (limestone, marble).
Let the reaction go for about 2 minutes before lowering a lit match into it. When
completed, throw them in the labeled water container; DO NOT CLOG THE
DRAIN!

4. Neutralizing Acids with Base: Using Indicators

In this experiment, you will make water acidic and then basic to see how the pH affects
a common indicator solution.

Add 25 mL of water and 3 drops of a phenolphthalein solution to a 100 mL beaker, and

then add 5 drops of 6 M hydrochloric acid. To this solution, add 10 percent sodium
hydroxide solution drop by drop until the indicator changes color. Once you’ve gotten
this color change, reverse it by adding more dilute acid dropwise.

5. Reaction of a Non-Metal Oxide and Water

In this section, you’ll investigate what happens when an oxide of a non-metal, sulfur,
reacts with water.

a. This part of the experiment must be done in the fume hood! Place a small lump of sulfur
in a deflagrating spoon (which looks like a ladle with a long handle) and set it on fire
with a Bunsen burner. Once the sulfur is burning, lower the spoon into a bottle
containing 15 mL of water; this will allow the fumes of combustion to fill the air space
of the bottle. After 2 minutes, remove the sulfur and cover the bottle with a glass plate.
Shake the bottle to mix the gas and water. Is the water acidic or basic?

b. In a test tube, generate carbon dioxide gas by treating marble chips with hydrochloric
acid (see section 3b). Bubble the gas into another beaker containing 10 mL of water, 2
drops of 10% sodium hydroxide, and a few drops of phenolphthalein indicator.

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C. Properties of Bases and Basic Solutions

1. Properties of ammonium and sodium hydroxides

a. Place three drops of concentrated ammonium hydroxide (used in “Windex”

cleaners) in 10 mL of water in a test tube. In another test tube, place three drops
of concentrated sodium hydroxide (used in “Drano” pipe cleaners) in 10 mL of
water. Rub a few drops of the diluted solution from each test tube onto your
fingers. What is the difference in feeling between the two solutions? Wash your
hands with water afterwards until your skin feels normal.

b. Test the two solutions with red and blue litmus papers and record the changes you
see.

c. Add two drops of phenolphthalein indicator to each test tube and record the changes
you see.

d. Determine the pH of each solution using a pH meter. Wash the electrode with dilute
acetic acid and then distilled water to clean it between every reading and after
you’re done.

2. The Reaction of Metal Oxides and Water

a. In three test tubes, place 10 mL of water, 2 drops of phenolphthalein, and a pinch

of calcium hydroxide, magnesium hydroxide, or calcium oxide. Record the color
changes.

b. In this last section, you will explore the reaction that occurs when you heat
limestone (“slaking lime”) to make a compound known as “quicklime”, which is
used in the manufacture of concrete:

Take a small piece of iron wire and wrap it around a small chip of calcium carbonate
(marble chip). Heat the chip until it is white hot with a Bunsen burner, for about 2
minutes. Let the chip cool and drop it into a beaker with 15 mL of water and a few
drops of phenolphthalein. Compare this result to an unheated chip.

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Data and Calculations for Experiment 7

A. Electrolytes and Instructor Demo

Place an “X” on the label that properly describes each compound below:
Non- Strong Weak
Electrolyte Electrolyte Electrolyte
1. Tap water
2. Distilled water
3. Sugar solution
4. NaCl solution
5a. Pure (glacial) acetic acid
5b. Diluted acetic acid
5c. Twice diluted acetic acid
6a. 1 M acetic acid
6b. 1 M HCl
6c. 1 M NH4OH
6d. 1 M NaOH
7a. NaNO3
7b. NaBr
7c. Ni(NO3)2
7d. CuSO4
7e. NH4Cl

1. What reaction occurs when barium sulfate and sulfuric acid are mixed?

2. Explain why the light becomes dimmer as two strong electrolytes are mixed with
each other.

3. Why does the light come back on after more of the electrolyte is added?

4. What happens to the glacial acetic acid as it is diluted? How does this explain the
changes in light intensity?

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B. Properties of Acids

1. Reactions of Acids with Metals

a) Which acids reacted with the magnesium?

b) Represent the reaction between the metal and ONE acid that occurred with an
equation.

2. Measurement of pH and Acidity

a) Acids turned the red litmus paper ____________ .

b) Acids turned the blue litmus paper ____________ .

c) What is the color of phenolphthalein in acidic solution? ____________

d) What is the pH of the 0.1 M solution? ____________

What is the pH of the 0.01 M solution? ____________

What is the pH of the 0.001 M solution? ____________

e) Which solution has the greatest concentration of H+?

f) Calculate the H+ concentration of a pH = 4.6 solution. Write the answer in

scientific notation.

3. Reactions of Acids with Carbonates and Bicarbonates

a) What is the name and formula of the gas formed in this reaction?

b) What happened to the burning stick when it was placed in the beaker?

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c) Write out the products of the reactions in a balanced equation:

NaHCO3 + HCl →

CaCO3 + HCl →

4. Neutralizing Acids with Base: Using Indicators

a) Write a balanced equation for the reaction of HCl and NaOH.

b) What happened when the acid was all neutralized?

5. Reaction of a Non-Metal Oxide and Water

a) Write a balanced equation for the reaction of sulfur and oxygen.

b) What happens when the product of the above reaction reacts with water? Write a
balanced equation that represents this reaction.

c) Write a balanced equation for the reaction of carbon dioxide and water.

d) How do you know that the product in the reaction above is acidic?

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C. Properties of Bases

1. Properties of ammonium and sodium hydroxides

a) What did the sodium hydroxide feel like?

b) What did the ammonium hydroxide feel like?

c) Bases turned the red litmus paper ____________ .

d) Bases turned the blue litmus paper ____________ .

e) What is the pH of the ammonium hydroxide solution? ________

f) What is the pH of the sodium hydroxide solution? ________

g) What is the concentration of H+ in the more basic solution? ________

2. The Reaction of Metal Oxides and Water

a) What is the color of phenolphthalein with CaO? ______________

What is the color of phenolphthalein with MgO? ______________

What is the color of phenolphthalein with Ca(OH)2? ______________

b) Write the balanced equations for the following reactions:

CaO + H2O →

MgO + H2O →

c) Marble is calcium carbonate (CaCO3). Write a balanced equation for the reaction
that occurs when you heat the marble chip.

d) Write a balanced equation for the reaction that occurs when you put the heated
marble chip in water.

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Experiment 8 – Acid/Base Titrations

Discussion

This experiment demonstrates an analytical technique known as titration, where a solution is

delivered from a buret until it completely consumes another solution in a flask. Consider the
following: 0

10

Acid-base titrations are an example of volumetric analysis, a 20

technique in which one solution is used to analyze another. The 30

solution used to carry out the analysis is called the titrant and is
40

delivered from a device called a buret, which measures the

volume accurately. The point in the titration at which enough 50

titrant has been added to react exactly with the substance being
determined is called the equivalence point (or stoichiometric
point). This point is often marked by the change in color of a
chemical called an indicator. The titration set-up is illustrated in
the schematic shown left.

First, the concentration of a base solution (standard) will be determined; this data will be used
to determine the concentration of unknown acid solutions. To standardize the NaOH solution,
it will be reacted with potassium hydrogen phthalate, KHC8H4O4 (abbreviated KHP). The
molar mass of KHP is 204.2 g/mol. The reaction of KHP with NaOH is known to be:

KHC8H4O4(aq) + NaOH(aq) → KNaC8H4O4(aq) + H2O(l)

Starting with a known mass of KHP and recording the volume of NaOH required to reach the
endpoint, the molarity of the base can be determined. The indicator to be used,
phenolphthalein, is colorless in acidic solution and rosy pink when slightly basic. Even though
the endpoint is slightly overshot in order to make the color change, the goal is to use as little
excess base as possible. Therefore, the titrated solution should be very pale pink, not bright
rosy red, at the endpoint.

Once the concentration of the NaOH solution is known, one can: (1) determine the
concentration of a hydrochloric acid solution and/or (2) determine the molarity and mass
percent of acetic acid in a sample of vinegar.

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Procedure

A. Standardization of Sodium Hydroxide

1. Measure out 1.000 to 1.200 g of KHP and add to a 125 mL Erlenmeyer flask.

2. Add approximately 30 mL of D.I. water to the flask. If some KHP is sticking to the
walls of the flask, rinse it down with D.I. water from a wash bottle.

3. Take another clean, dry 250 mL Erlenmeyer flask to the hood and obtain approximately
100 mL of NaOH base. Be certain to keep the base solution stoppered when not in use.

4. Obtain a clean 50 mL buret. Carefully fill the buret with base, making sure that no air
bubbles are present. Run some of the base solution through the buret tip to remove the
air pocket in the tip.

5. Record the initial buret reading (x.xx mL) in the data section. When you read a buret,
the line of sight must be level with the BOTTOM of the meniscus to avoid error. The
top of the buret reads 0.00 mL; the bottom reads 50.00 mL. Notice the numbers increase
going down. Take note of this when reading the numbers. Your instructor will
demonstrate.

6. Add 2 to 3 drops of phenolphthalein indicator solution to the 125 mL Erlenmeyer flask

containing KHP and water. Swirl your acid solution to mix well.

7. Place the flask under the tip of the buret. A piece of white paper under the flask makes
it easier to see the pale pink color at the endpoint. Open the valve and allow base to
drip from the buret into the flask. Swirl continually to mix the solutions. As you get
closer to the endpoint, the solution will begin to show pink color that goes away when
you mix. Slow the rate of base addition to one drop at a time, mixing the solutions well
after every drop. If you splash the solution up onto the sidewalls of the flask, spray a
stream of water from your wash bottle over the inside of the flask. The extra water that
mixes into your acid sample will not affect your results. Once the addition of ONE drop
of base changes the solution from colorless to pale pink, close the buret valve and make
certain that the pale pink color lasts for at least 30 seconds. If so, record the final buret
reading. If not, carefully add one more drop of base from the buret valve until the pale
pink color persists for 30 seconds or longer. If at the end of your trial the color is bright
rosy red, you have overshot the endpoint. Make a note in your data if you overshoot

8. Discard the titrated solution into the sink, rinse the flask with D.I. water, and then titrate
another new sample of KHP following the same procedure above. Do at least TWO
successful titrations that achieve a pale pink color of the indicator.

9. Calculate the average molarity of the base from your two successful trials and check
with your instructor for verification before proceeding to part B.

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B. Molarity Determination of a Hydrochloric Acid Solution

1. From the hood, half fill a medium test tube with the unknown hydrochloric acid. Using
a volumetric pipet, transfer 10.00 mL of the acid sample to a clean Erlenmeyer flask
(your instructor will demonstrate).

2. Add 2 to 3 drops of phenolphthalein indicator solution and approximately 25 mL of

D.I. water to the flask containing the 10.00 mL acid and swirl.

3. Refill the buret with NaOH and record the initial buret reading.

4. Place the flask under the buret and add base until you reach the endpoint as outlined in
Part A above. Record the final buret reading, discard the sample in the sink, and repeat
the titration until you have TWO successful trials. Determine the average molarity of
the hydrochloric acid solution from your two successful trials and check with your
instructor for verification.

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Data and Calculations for Experiment 8

A. Standardization of NaOH(aq)

Data Table for Part A

Sample 1 Sample 2
Mass of flask and KHP
Mass of empty flask
Mass of KHP
Initial buret reading
Final buret reading
Volume of base used

1. Moles of acid (KHP, Molar mass = 204.2)

Sample 1:

Sample 2:

2. Moles of base used to neutralize acid

Sample 1:

Sample 2:

3. Molarity of base (NaOH)

Sample 1:

Sample 2:

4. Average Molarity of Base (to be used in Part B)

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B. Molarity Determination of HCl(aq)

Volume of HCl solution used: ___________

Data Table for Part B

Sample 1 Sample 2
Initial buret reading
Final buret reading
Volume of base used

1. Moles of base (NaOH) used

Sample 1:

Sample 2:

2. Moles of acid used to neutralize base

Sample 1:

Sample 2:

3. Molarity of acid (HCl)

Sample 1:

Sample 2:

4. Average Molarity of Acid

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Questions

1. A titration required 13.42 mL of 0.1638 M NaOH solution. How many moles of NaOH
were in this volume?

2. A student weighed a sample of KHP and found it weighed 1.396 g. Titration of this KHP
required 21.36 mL of base (NaOH). Calculate the molarity of the base.

3. Write and balance the equation for the neutralization of a sulfuric acid solution of unknown
concentration by sodium hydroxide. Calculate the molarity of an unknown sulfuric acid
solution if a 25.0 mL sample of the acid solution consumes 27.2 mL of 0.138 M NaOH
solution in a titration.

4. What might happen to your calculated NaOH molarity if you used tap water instead if D.I.
water to dissolve the KHP crystals or to rinse down the walls of the flask during the
titration? Hint: Tap water contains some calcium carbonate.

5. In your own words, use the back of this page to write a cohesive, well-written summary of
the background material and underlying chemical principles pertinent to this experiment.
(For additional guidelines on writing this introduction, please refer to the Moorpark
College Chemistry Department Laboratory Report Rubric found in the lab manual and
department website.)

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Experiment 9 – Structure in Inorganic & Organic Compounds

Discussion

The Valence Shell Electron Pair Repulsion Theory (VSEPR) states that bonds and lone pairs
are regions of high electron density in an atom that repel each other until they get as far apart
as possible. This effect determines the atom’s geometry and bond angles. Two regions will be
180° apart, three regions will be 120° apart, and four regions will be 109.5° apart.

Geometry Determination

1. Determine the Lewis dot structure of the molecule or ion.

2. For each central atom in the structure, determine the areas of electron density that lie
directly on that atom. An area of electron density may be:
a. a lone pair that lies on the central atom. (Lone pairs on other atoms don’t count.)
b. a single bond.
c. a double bond.
d. a triple bond.
3. Assign geometry according to the table on the next page.

Procedure

For each of the ions or molecules listed:

1. Draw the Lewis dot structure, including all resonance where appropriate.
2. Use the model kit to build the structure.
• Use yellow balls for hydrogens.
• Use black balls for other atoms.
• Use short sticks for nonbonded electron pairs
• Use long sticks for single bonds.
• Use springs for double and triple bonds. Two springs form a double bond. Three
springs form a triple bond.
3. Sketch the shape of the structure in three dimensions. This is called the VSEPR structure.
4. Draw dipole moments on the VSEPR structure to show all polar bonds.
5. Give the name of the molecular geometry.
6. State whether the molecule is polar, nonpolar, or ionic.
7. Determine the approximate bond angle on the central atom(s).

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# of Geometry
# of # of lone and bond
areas bonds pairs angles Example
4 2 2 Angular or
O
bent (109.5°)
H H
4 3 1 Pyramidal
(109.5°) N
H
H
H
4 4 0 Tetrahedral H
(109.5°)
N
H
H
H

3 2 1 Bent
(120°) S S
O O O O

2 resonance forms
3 3 0 Trigonal
O O O
(120°)
N N N
O O O O O O

3 resonance forms
2 2 0 Linear H C N
(180°)
1 any Linear
(Must be O O
three or more
atoms to form
an angle.)

Notice the convention for drawing bonds in 3-D space, where:

 the wedge ( ) represents a bond coming out of the paper, and
 the dash ( ) represents a bond going behind the paper.

Finally, isomers will also be studied, or molecules having the same chemical formula
but different connectivity of the atoms. Be sure not to confuse this phenomenon with
resonance, where atoms are in the same place but electrons are delocalized throughout. For
example, two isomers are possible for a molecule with the formula C4H10:
H
H H H H H H C H H

H C C C C H H C C C H

H H H H H H H

Chemistry M11 Laboratory Manual Page 49

 Number of Polar? Bond angle
Lewis dot structure VSEPR structure Molecular
Formula valence Nonpolar? on central
(including ALL resonance) (with dipole moments) Geometry
electrons Ionic? atom(s)

I2

Chemistry M11 Laboratory Manual

NO–
Name: _________________________________

CO

CH3NH2

Page 50
Section: _____________________
 Number of Polar? Bond angle
Lewis dot structure VSEPR structure Molecular
Formula valence Nonpolar? on central
(including ALL resonance) (with dipole moments) Geometry
electrons Ionic? atom(s)

H2S

Chemistry M11 Laboratory Manual

PBr3
Name: _________________________________

ClO4–

CS2

Page 51
Section: _____________________
 Number of Polar? Bond angle
Lewis dot structure VSEPR structure Molecular
Formula valence Nonpolar? on central
(including ALL resonance) (with dipole moments) Geometry
electrons Ionic? atom(s)

CHCl3

Chemistry M11 Laboratory Manual

PO3–3
Name: _________________________________

PO4–3

CH2O

Page 52
Section: _____________________
 Number of Polar? Bond angle
Lewis dot structure VSEPR structure Molecular
Formula valence Nonpolar? on central
(including ALL resonance) (with dipole moments) Geometry
electrons Ionic? atom(s)

SO3

Chemistry M11 Laboratory Manual

SO3–2
Name: _________________________________

SO4–2

SCN–1

Page 53
Section: _____________________
 Number of Polar? Bond angle
Lewis dot structure VSEPR structure Molecular
Formula valence Nonpolar? on central
(including ALL resonance) (with dipole moments) Geometry
electrons Ionic? atom(s)

NO2–

Chemistry M11 Laboratory Manual

HCOOH
Name: _________________________________

BrO3–

IO2–

Page 54
Section: _____________________
 Number of Polar? Bond angle
Lewis dot structure VSEPR structure Molecular
Formula valence Nonpolar? on central
(including ALL resonance) (with dipole moments) Geometry
electrons Ionic? atom(s)

CH2Cl2

Chemistry M11 Laboratory Manual

C2F2
Name: _________________________________

C2F4

C2F6

Page 55
Section: _____________________
 Number of Polar? Bond angle
Formula Lewis dot structure VSEPR structure Molecular
valence Nonpolar? on central
(including ALL resonance) (with dipole moments) Geometry
electrons Ionic? atom(s)

C2H2Br2
(3 isomers)

Chemistry M11 Laboratory Manual

Name: _________________________________

C2H6O
(2 isomers)

C5H12
(3 isomers)

Page 56
Section: _____________________
Name: _________________________________ Section: _____________________

Experiment 10 – Stereochemistry & Use of Molecular Models

Discussion and Procedure

This lab will help you discover and learn about stereochemistry and the various terms
associated with it. You will be provided with a model kit. Bring your course guide to help you
with some of these concepts. Answer the questions below each section at the end of this lab
(to be submitted to your instructor).

Construct a model (called structure A) in which a carbon atom (represented by a black ball)
has four different colored balls attached to it – white, green, red, and blue – representing four
different substituents attached to the central carbon. The white ball represents hydrogen, the
green ball represents chlorine, the red ball represents bromine, and the blue ball represents
iodine. The carbon of structure A is called a stereocenter.

Q-1) Using wedges and dashes, draw this molecule in at least four different orientations. In
each orientation that you draw, the same two atoms should NOT both be on wedges and
dashes. Practice rotating the molecule in your hands and on paper, until you are
comfortable with viewing molecules in three dimensions.

Q-2) Does molecule A have a plane of symmetry?

Replace the red ball with a green one.

Q-3) Does the revised model have a plane of symmetry now? Find an orientation in which it
is easy to draw this plane of symmetry, then draw the molecule using wedges and dashes
and draw a dotted line representing the plane of symmetry.

Now, rebuild structure A.

Put the model on a flat surface so that the white ball points up. Look straight down the model
and, starting with the green ball and proceeding clockwise, record the order of the balls. Now,
construct a model (structure B) which is a mirror image of structure A. Place structure B on a
flat surface adjacent to structure A with the white ball of both pointing at the ceiling.

Q-4) Try superposing (aligning) all five atoms at the same time. Can you superpose structure
B and structure A? How many atoms can you superpose at one time? Try to improve on
this number until you think that you cannot get any more atoms to superpose at any one
time.

Q-5) Are structure A and structure B identical?

Q-6) How do the structures differ?

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The two structures A and B are chiral molecules. A chiral molecule does not have a plane of
symmetry and has a non-superposable mirror image. The pair of structures that are non-
superposable mirror images are called enantiomers. These two compounds differ only in the
way they rotate plane-polarized light. Each enantiomer is said to be optically active.

On both structures A and B, replace the red ball with a green ball and call the new structures
C and D.

Q-7) Are structures C and D still mirror images of each other?

Q-8) Do C and D have internal planes of symmetry?

Q-9) Can you superpose structures C and D? Are these molecules identical or different?

Structures C and D represent achiral molecules. Achiral molecules have a superposable mirror
image, a plane of symmetry, and do not rotate plane-polarized light. Achiral molecules are
optically inactive. (Remember: the prefix a- means the same as non-)

The R/S convention is used to designate the configurations at stereocenters. The attached atoms
to the stereocenter are arranged in order of increasing atomic number. Thus, higher atomic
number means higher priority. If two atoms have the same priority, you move to the next atom
out and compare those atoms. Continue this until you break the tie. Look at the molecule from
the side opposite the group with the lowest priority. If you count the highest to lowest priority
and you go in a clockwise direction, you have the R configuration. If you move
counterclockwise, the stereocenter is the S configuration.

Rebuild structures A and B. Make sure that B is the mirror image of A.

In our model kits, the black balls represent carbon atoms, the white balls represent hydrogen,
the green balls represent chlorine, the red balls represent bromine, and the blue balls represent
iodine.

Q-10) Using wedges and dashes, draw molecules A and B.

Working with structure A, interchange any two balls attached to the stereocenter. Call this
molecule E.

Q-11) What happened to the configuration at the stereocenter? How does molecule E compare
to molecule B?

In your molecule E, change two different balls (not the same ones as you did in the previous
step). Call this molecule F.

Q-12) How does molecule F compare to molecule B? How does it compare to your original
molecule A?

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Q-13) Repeat this process by swapping two groups at a time several more times. How many
different stereoisomers do you find through this process?

Build a model of (R)-2-chlorobutane and a model of (S)-2-chlorobutane

Q-14) Using your models, determine which of the structures below have the R configuration
and which have the S configuration. To verify your answer, rotate each model to align
it with the structure that is drawn below. Label each structure in your Report Form
along with the appropriate R or S designations.

Two compounds with the same molecular formula but a different arrangement in space are
called stereoisomers. A stereoisomer that has a non-superposable mirror image is called an
enantiomer. A stereoisomer with a non-superposable non-mirror image is called a
diastereomer. Diastereomers usually have two or more stereocenters.

Now build the following two molecules:

(2R, 3R)-2,3-dichlorobutane = Molecule G

(2S, 3S)-2,3-dichlorobutane = Molecule H

Label each model with a piece of tape that has the molecule’s letter (G or H).

Q-15) Determine the relationship between molecules G and H.

Please put your model kit away exactly the way that you found it.

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Data and Questions for Experiment 10

1. Using wedges and dashes, draw this molecule in at least four different orientations. In
each orientation that you draw, the same two atoms should NOT both be on wedges and
dashes. Practice rotating the molecule in your hands and on paper, until you are
comfortable with viewing molecules in three dimensions.

2. Does molecule A have a plane of symmetry? Briefly explain.

3. Does the revised model have a plane of symmetry now? Find an orientation in which it is
easy to draw this plane of symmetry, then draw the molecule using wedges and dashes and
draw a dotted line representing the plane of symmetry.

4. Try superposing (aligning) all five atoms at the same time. Can you superpose structure B
and structure A? How many atoms can you superpose at one time? Try to improve on this
number until you think that you cannot get any more atoms to superpose at any one time.

5. Are structure A and structure B identical? Mark ONE: Yes No

6. How do the structures differ?

7. Are structures C and D still mirror images of each other? Yes No

8. Do C and D have internal planes of symmetry? Yes No

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9. Can you superpose structures C and D? Are these molecules identical or different?
 Yes  No  Identical  Different

10. Using wedges and dashes, draw molecules A and B.

11. What happened to the configuration at the stereocenter? How does molecule E compare to
molecule B?

12. How does molecule F compare to molecule B? How does it compare to your original
molecule A?

13. Repeat this process by swapping two groups at a time several more times. How many
different stereoisomers do you find through this process?

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14. Using your models, determine which of the structures below have the R configuration and
which have the S configuration. Label each structure below with the appropriate R or S
designations.

15. Determine the relationship between molecules G and H.

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Experiment 11 – Paper Chromatography

Discussion

In addition to recrystallization and distillation, chromatography can also be used to separate

the components of a homogeneous mixture. Initially, chromatography was used to separate
colored substances, hence the name (Greek chroma, color). The colors of the components of
the mixture are observed as they separate. This technique can also be used with colorless
substances if they fluoresce when exposed to ultraviolet light or if they react with a second
reagent to produce colored products.

Separation of substances by chromatography depends on the differences between the

adsorptive characteristics of the substances with respect to a stationary phase material such as
paper. The components of the mixture are adsorbed onto the stationary phase. Continued
passage of a solvent in the stationary phase dissolves the adsorbed components of the mixture
and moves them along the paper, known as the mobile phase. Each component moves at its
own rate; after a given time interval, each component has moved a different distance across
the stationary phase.

In this experiment, amino acids will be placed on a sheet of paper and the solvent allowed to
travel along the paper by capillary action for a given period of time. The paper serves as the
stationary phase, and the amino acids will move along the paper at rates that depend on their
structures. Students will determine the distance traveled by certain amino acids; ultimately, an
unknown mixture will be analyzed for amino acid(s) present. The ratio of the distance traveled
by an amino acid relative to that traveled by the solvent is the Rf value for the amino acid.

distance traveled by compound

Rf =
distance traveled by solvent

Since amino acids are colorless, identification of their positions at the end of the experiment is
necessary. Ninhydrin will be used to develop a spot of color at the point to which each amino
acid has moved.

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Procedure

CAUTION! 2% ninhydrin in ethanol will strongly stain the amino acids on your skin.
Avoid spilling the ninhydrin solution on yourself.

Prepare a solution of 10 mL 2% aqueous ammonia in 20 mL 2-propanol. The solution should

be placed in a 600 mL beaker and covered with aluminum foil. This is your solvent that will
be used to flush the known and unknown mixtures along the stationary phase.

Obtain (3) 5-mL beakers. Fill the first beaker with a few drops (no more than 2 mL) of 0.05 M
aspartic acid solution in 1.5% hydrochloric acid. Now fill the second beaker with a few drops
(no more than 2 mL) of 0.05 M glycine solution in 1.5% hydrochloric acid, and the third beaker
with a few drops (no more than 2 mL) of 0.05 M tyrosine solution in 1.5% hydrochloric acid.
Also obtain a labeled vial which contains an unknown mixture from your instructor. Make
certain to record your unknown mixture code.

You will be provided with a sheet of Whatman No. 1 filter paper, already cut to size 10 x 24
cm. Using a pencil, lightly draw a solid line along the long axis 2 cm from the bottom edge
(see Figure One below). Along this line, place eight ‘x’ marks at equal intervals 2.5 cm apart,
beginning with the first mark 2.5 cm from the short left edge of the paper. The prescribed
distance of 2.5 cm between marks will allow proper placement of all the ‘x’ marks. Notice the
order of the various amino acids followed by the unknown mixture; you will repeat the order
of the amino acids and the unknown for confirmation a second time along the paper.

Figure One. Preparation of Chromatographic Sheet

2.5 cm
x x x x x x x x
2 cm
Aspartic Acid

Aspartic Acid
Glycine

Tyrosine

Glycine

Tyrosine
Unknown

Unknown

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Using separate capillary tubes for each mixture, place a small drop of each solution at the two
respective positions along the line on the filter paper as shown in Figure One. Make sure each
spot of solution on the paper is not larger than 2 mm by quickly withdrawing the capillary from
the paper when time you touch it. After spotting all samples on the paper, allow the paper to
dry in the air for 10 minutes.

Roll the paper into a cylinder such that the line is on the bottom outside of the cylinder. Staple
the ends together to hold the cylinder in shape. Place the staples about 4 cm from each edge of
the cylinder. Do not allow the edges of the paper to touch when the staples are put in. A small
gap in the cylinder is necessary.

Placed the stapled chromatogram paper into the 600 mL beaker, base line down, along the
solvent surface BUT NOT COVERED BY IT. Avoid splashing the solvent on the paper. Make
sure the paper does not touch the sides of the beaker. Allow the solvent front to migrate up to
1 cm below the edge of the paper (top) for at least 90 minutes. Afterwards, remove the paper
from the cylinder, mark the edge of the wet part of the paper, and allow it to air dry on the lab
bench top. Once the cylinder is essentially dry, remove the staples and hang it in the hood.
Your instructor will spray the paper with a solution of 2% ninhydrin in ethanol. After the spray
dries, place the paper in an oven at 100 ºC for 10-15 minutes. Note the spots and circle each
one. Measure the distances from the ‘x’ to each spot and the distance traveled by the solvent.
The distance traveled by the solvent is the distance from the liquid level in the beaker to the
edge of the wet portion of the paper. Calculate the Rf values and determine the identity of your
unknown.

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Data and Calculations for Experiment 11

UNKNOWN CODE: _________________

Solution Distance Traveled Distance Traveled Rf value

by Amino Acid by Solvent (cm)
(cm)
Aspartic Acid
Glycine
Tyrosine
Unknown

Post-lab Questions

1. How might it be possible to quantitatively determine the composition of an amino acid

mixture? You may need to research this question a bit!

2. If two amino acids have the same Rf values in 2-propanol, how might they be separated?

3. Identify the component(s) of your mixture, then draw the structure(s) of the amino acid(s)
present. Refer to your Biochemistry notes from lecture for the structures of the various
amino acids.

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Experiment 11 – Identification of Hydrocarbons

Discussion

The number of known organic compounds totals into the millions. Of these compounds, the
simplest types are those that contain only hydrogen and carbon atoms. These are known as
hydrocarbons. Because of the number and variety of hydrocarbons that can exist, some means
of classification is necessary.

One means of classification depends on the way in which carbon atoms are connected. Chain
aliphatic hydrocarbons are compounds consisting of carbons linked either in a single chain or
in a branched chain. Cyclic hydrocarbons are aliphatic compounds that have carbon atoms
linked in a closed polygon (also referred to as a ring). For example, hexane (single) and 2-
methylpentane (branched) are chain aliphatic molecules, while cyclohexane is a cyclic
aliphatic compound.

hexane 2-methylpentane cyclohexane

Another means of classification depends on the type of bonding that exists between carbons.
Hydrocarbons that contain only carbon-to-carbon single bonds are called alkanes. These are
also referred to as saturated molecules. Hydrocarbons containing at least one carbon-to-carbon
double bond are called alkenes, and compounds with at least one carbon-to-carbon triple bond
are called alkynes. Alkenes and alkynes are referred to as unsaturated molecules. Finally, a
class of cyclic hydrocarbons that contain a closed loop (sextet) of electrons is called aromatic.
With so many compounds possible, identification of the bond type is an important step in
establishing the molecular structure. Quick, simple tests on small samples can establish the
physical and chemical properties of the compounds by class.

Some of the observed physical properties of hydrocarbons result from the nonpolar character
of the compounds. In general, hydrocarbons do not mix with polar solvents such as water or
ethanol (ethyl alcohol). On the other hand, hydrocarbons mix with relatively nonpolar solvents
such as ligroin (a mixture of alkanes), carbon tetrachloride (CCl4), or dichloromethane
(CH2Cl2). Because the density of most hydrocarbons is less than that of water, they will float.
Crude oil and crude oil products (home heating oil and gasoline) are mixtures of hydrocarbons;
when spilled on water, these substances spread quickly along the surface because they are
insoluble in water.

The chemical reactivity of hydrocarbons is determined by the type of bond in the compound.
Unsaturated hydrocarbons (i.e., alkenes and alkynes) react by addition of reagents to the
double or triple bonds. The addition products become saturated, with fragments of the reagent
becoming attached the carbons of the multiple bond. Aromatic compounds, with a higher
carbon-to-hydrogen ratio than nonaromatic compounds, undergo substitution in the presence
of catalysts rather than an addition reaction.

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1. Reaction with bromine. Unsaturated hydrocarbons react rapidly with bromine in a

solution of carbon tetrachloride or cyclohexane. The reaction is the addition of the
elements of bromine to the carbons of the multiple bonds.

Br

+ Br2
Br
Red Colorless

Br Br

+ 2Br2
Br Br
Red Colorless

The bromine solution is red; the product that has the bromine atoms attached to carbon
is colorless. Thus, a reaction has taken place when there is a loss of color from the
bromine solution and a colorless solution remains. Because alkanes have only single
C–C bonds present, no reaction with bromine is observed; the red color of the reagent
would persist when added. Aromatic compounds resist addition reactions because of
their “aromaticity”: the possession of a closed loop (sextet) of electrons which imparts
extreme stability. These compounds can react with bromine but require the presence of
a catalyst such as iron fillings or aluminum chloride.

2. Reaction with concentrated sulfuric acid. Alkenes react with cold concentrated sulfuric
acid by addition. Alkyl sulfonic acids form as products and are soluble in H2SO4;
subsequent water work-up results in an “–OH” on the more substituted carbon (as
demonstrated in lecture).

OH
H2O
+ H2SO4

Saturated hydrocarbons are unreactive (additions are not possible); alkynes react
slowly and require a catalyst (H2SO4); due to their inherent stability, aromatic
compounds are also unreactive.

3. Reaction with potassium permanganate. Dilute or alkaline solutions of KMnO4 oxidize

unsaturated compounds. Alkanes and aromatic compounds are generally unreactive.
Evidence that a reaction has occurred is observed by the loss of the purple color of
KMnO4 and the formation of the brown precipitate manganese dioxide, MnO2.

OH
3 + 2KMnO4 + 4H2O 3 + 2MnO2 + 2KOH
Purple OH Brown

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Note that the product formed (which contains two “–OH” groups) is called a
glycol.

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Procedure

Assume the organic compounds are highly flammable. Use only small quantities. Keep away
from open flames. Assume the organic compounds are toxic and can be absorbed through the
skin. Avoid contact; wash if any chemical spills on your person. Handle concentrated sulfuric
carefully. Flush with water if any spills on your person. Potassium permanganate and bromine
are toxic; bromine solutions are also corrosive. Although the solutions are diluted, they may
cause burns to the skin. Wear gloves when working with these chemicals. Also consider the
following:

1. The hydrocarbons hexane, cyclohexene, and toluene (alkane, alkene and aromatic,
respectively) are available in dropper bottles.

2. The reagents 1% Br2 in cyclohexane, 1% aqueous KMnO4, and concentrated H2SO4

are available in dropper bottles.

3. Unknowns are in dropper bottles labeled A, B, and C. They may include an alkane, an
alkene, and/or an aromatic compound.

4. Test tubes will be suitable for all the tests; mix thoroughly.

5. Dispose of all organic wastes as directed by the instructor. Do not pour them into the
sink!

Physical Properties of Hydrocarbons

1. Water solubility of hydrocarbons. Label six test tubes with the name of the substance
to be tested. Place into each test tube 5 drops of the appropriate hydrocarbon: hexane,
cyclohexene, toluene, unknown A, unknown B, and unknown C. Add about 5 drops of
water dropwise into each test tube. Water is a polar solvent. Is there any separation of
components? Which component is on the bottom; which component is on the top? Mix
the contents. What happens when the contents are allowed to settle? What do you
conclude about the density of the hydrocarbon? Is the hydrocarbon more dense than
water or less dense than water? Record your observations. Save these solutions for
comparison with the next part.

2. Solubility of hydrocarbons in ligroin. Label six test tubes with the name of the
substance to be tested. Place into each test tube 5 drops of the appropriate
hydrocarbons: hexane, cyclohexene, toluene, unknown A, unknown B, and unknown
C. Add about 5 drops of ligroin dropwise into each test tube. Ligroin is a nonpolar
solvent. Is there a separation of components? Is there a bottom layer and a top layer?
Mix the contents. Is there any change in the appearance of the contents before and after
mixing? Compare these test tubes with those from the previous part. Record your
observations. Can you make any conclusion about the density of the hydrocarbons from
what you actually see?

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Chemical Properties of Hydrocarbons

1. Reaction with bromine. Results provided on data sheet.

2. Reaction with KMnO4. Label six clean, dry test tubes with the name of the substance to
be tested. Place into each test tube 5 drops of the appropriate hydrocarbon: hexane,
cyclohexene, toluene, unknown A, unknown B, and unknown C. Carefully add
(dropwise) 1% aqueous KMnO4 solution; after each drop, shake to mix the solutions.
Keep count of the number of the drops needed to have the color of the permanganate
solution persist; do not add more than 10 drops. Record your observations.

3. Reaction with concentrated H2SO4. Label six clean, dry test tubes with the name of the
substance to be tested. Place into each test tube 5 drops of the appropriate hydrocarbon:
hexane, cyclohexene, toluene, unknown A, unknown B, and unknown C. Place all of
the test tubes in an ice bath. Wear gloves and carefully add (with shaking) 3 drops of
cold, concentrated sulfuric acid to each test tube. Note whether the solution has become
homogeneous or whether a color is produced. (The evolution of heat, the formation of
a homogeneous solution, or the appearance of a color is evidence that a reaction has
occurred.) Record your observations.

4. Unknowns: By comparing the observations you made for your unknowns with that of
the known hydrocarbons, you can identify unknowns A, B, and C. Record their
identities on your data sheet.

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Data and Calculations for Experiment 12

Physical Properties of Hydrocarbons

Solubility: Does the hydrocarbon mix with the solvent, soluble, or not mix with solvent,
insoluble? Use the observations you make for the solubility tests and determine whether the
hydrocarbons are polar or nonpolar substances.

Density: For water, is the density greater than water (sinks) or less than water (floats)? For
ligroin, can you tell anything about the relative densities?

H2 O Ligroin

Hydrocarbon Solubility Density Solubility Density

Hexane

Cyclohexene

Toluene,

Unknown A

Unknown B

Unknown C

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Chemical Properties of Hydrocarbons

Hydrocarbon Bromine Test* KMnO4 Test H2SO4 Test

Hexane Red

Cyclohexene Colorless

Toluene,
Red

Unknown A Red

Unknown B Colorless

Unknown C Red

*The results of the bromine test have been provided for you.

Unknown A is ______________________.

Unknown B is ______________________.

Unknown C is ______________________.

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Questions

1. Below are four organic compounds. The reagent shown is added to the compound. Based
on your studies in this lab, determine the products (if any) that you should observe when
the reactants below are mixed together:
A. + Br2

B. + KMnO4

C. H2O
+ H2SO4

D. + KMnO4

2. A student has two compounds in two separate bottles but with no labels on either one. One
is an alkane, octane (C8H18); the other is 1-hexene (C6H12), an alkene. Based on your
observations in this experiment, what should you see in the following tests?

Octane 1-Hexene
A. Water solubility

B. Ligroin solubility

C. Density versus water

D. Bromine test

E. Permanganate test

3. An unknown compound, believed to be a hydrocarbon, showed the following behavior: no

heat or color appeared when sulfuric acid was added; permanganate solution remained
purple; and the red color of bromine solution was lost only after a catalyst was added. From
the compounds below, circle the ONE that fits the observations.

OR OR OR

4. In your own words, write a one-half page, well-written abstract of the entire experiment,
making sure to briefly state the overall purpose or goal as well as any conclusions. (For
additional guidelines on writing this abstract, please refer to the Moorpark College
Chemistry Department Laboratory Report Rubric found in the lab manual and
department website.)

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Experiment 13 – Properties of Amines and Amides

Discussion

Amines and amides are two classes of organic compounds that contain nitrogen. Amines
behave as organic bases and may be considered derivatives of ammonia. Amides are
compounds that have a carbonyl group connected to a nitrogen atom and are neutral. In this
experiment, you will learn about the physical and chemical properties of some members of the
amine and amide families.

If the hydrogens of ammonia are replaced by alkyl or aryl groups, amines result. Depending
on the number of carbon atoms bonded directly to nitrogen, amines are classified as either
primary (one carbon atom) secondary (two carbon atoms), or tertiary (three carbon atoms).
Consider the following examples:

NH2 NHCH3 N(CH3)2

Aniline N-Methylaniline N,N-Dimethylaniline

(1° amine) (2° amine) (3° amine)

There are a number of similarities between ammonia and amines that carry beyond the structure
such as odor. The smell of amines resembles that of ammonia but is not as sharp. However,
amines can be quite pungent. Anyone handling or working with raw fish knows how strong
the amine odor can be: raw fish contains low molecular weight amines such as dimethylamine
and trimethylamine. Other amines associated with decaying flesh have names suggestive of
their odors: consider putrescine and cadaverine shown below.

NH2CHCH2CH2CH2NH2 NH2CHCH2CH2CH2CH2NH2
Putrescine Cadaverine

The solubility of low molecular weight amines in water is high. In general, if the total number
of carbons attached to nitrogen is four or less, the amine is water soluble; amines with a carbon
content greater than four are water insoluble. However, all amines are soluble in organic
solvents such as diethyl ether or dichloromethane.

Because amines are organic bases, water solutions show weakly basic properties. If the basicity
of aliphatic amines and aromatic amines is compared to that of ammonia, aliphatic amines are
stronger than ammonia, while aromatic amines are weaker. Amines characteristically react
with acids to form ammonium salts; the nonbonded electron pair on nitrogen bonds the
hydrogen ion:

RNH2 + HCl  RNH3+Cl–

Amine Ammonium Salt

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If an amine is insoluble, reaction with an acid produces a water-soluble salt. Because

ammonium salts are water soluble, many drugs containing amines are prepared as ammonium
salts. After working with fish in the kitchen, a convenient way to rid one’s hands of fish odor
is to rub a freshly cut lemon over the hands. The citric acid found in the lemon reacts with the
amines found on the fish; a salt forms that can be easily rinsed away with water.

Amides are carboxylic acid derivatives. The amide group is recognized by the nitrogen
connected to the carbonyl group. Amides are neutral compounds. Under suitable conditions,
amide formation can take place between an amine and a carboxylic acid. Along with ammonia,
primary and secondary amines yield amides with carboxylic acids. For example:

O O
heat
CH3NH2 + CH3 + H2O
H3C OH H3C N
H

Hydrolysis of amides can take place in either acid or base. Primary amides hydrolyze in acid
to ammonium salts and carboxylic acids. Neutralization of the acid and ammonium salts
releases ammonia, which can be detected by odor or by litmus.

O O
+ HCl + H2O + NH4Cl
R NH2 R OH
NH4Cl + NaOH → NH3 + NaCl + H2O

Secondary and tertiary amides would release the corresponding alkyl ammonium salts which,
when neutralized, would yield the amine.

In base, primary amides hydrolyze to carboxylic acid salts and ammonia. The presence of
ammonia (or amine from corresponding amides) can be detected similarly by odor or litmus.
The carboxylic acid would be generated by neutralization with acid.

O O
+ NaOH + NH3
R NH2 R O Na+

O O
+ HCl + NaCl
R O Na+ R OH

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Procedure
Caution: Amines are toxic chemicals. Avoid excessive inhaling of the vapors and use gloves
to avoid direct skin contact. Anilines are more toxic than aliphatic amines and are readily
absorbed through the skin. Wash any amine or aniline spill with large quantities of water.
Diethyl ether is extremely flammable. Be certain there are NO open flames in the immediate
area. Discard all solutions in properly labeled organic waste containers.

Properties of Amines
1 Place 5 drops of liquid or 0.1 g of solid from the compounds listed in the following table
into labeled clean, dry test tubes (100 x 13 mm).
Test Tube No. Nitrogen Compound
1 6 M NH3
2 Triethylamine
3 Aniline
4 N,N-Dimethylaniline
5 Acetamide
2 Carefully note the odors of each compound. Do not inhale deeply. Merely wave your
hand across the mouth of the test tube toward your nose (i.e., wafting motion) in order
to note the odor. Record your observations on your data sheet.
3 Add 2 mL of distilled water to each of the labeled test tubes. Mix thoroughly by sharply
tapping the test tube with your finger. Note on the data sheet whether the amines are soluble
or insoluble.
4 Take a glass rod and test each solution for its pH. Carefully dip one end of the glass rod
into a solution and touch a piece of pH paper. Between each test, be sure to clean and dry
the glass rod. Record the pH by comparing the color of the paper with the chart on the
dispenser.
5 Carefully add 2 mL of 6 M HCl to each test tube. Mix thoroughly by sharply tapping the
test tube with your finger. Compare the odor and solubility of this solution with previous
observations.
6 Place 5 drops of liquid or 0.1 g of solid from the compounds listed in the table into labeled
clean, dry test tubes (100 x 13 mm). Add 2 mL of diethyl ether to each test tube. Stopper
with a cork and mix thoroughly by shaking. Record the observed solubilities.
7 IN THE HOOD, carefully place a drop of triethylamine and a drop of concentrated HCl on
a watch glass, side by side without touching. Record your observations.

Hydrolysis of Acetamide
1. Dissolve 0.5 g of acetamide in 5 mL of 6 M H2SO4 in a large test tube (150 x 18 mm). Heat
the solution in a boiling water bath for 5 min.
2. Hold a small strips of moist pH paper just inside the mouth of the test tube WITHOUT
touching the sides, note any changes in color; record the pH reading. Remove the test tube
from the water bath, holding it with a test tube holder. Carefully note any odor.
3. Place the test tube in an ice water bath until cool to the touch. Now carefully add, dropwise
with shaking, 6 M NaOH to the cool solution until basic. (You will need more than 7 mL
of base). Hold a piece of moist pH paper just inside the mouth of the test tube without
touching the sides. Record the pH reading. Carefully note any odor.

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Data and Calculations for Experiment 13

Properties of amines

Odor Solubility pH
Original Soln with HCl H2O Ether HCl H2O

6 M NH3

Triethylamine

Aniline

N,N – Dimethylaniline

Acetamide

Triethylamine and concentrated hydrochloric acid observation:

Write the chemical equation for the reaction of triethylamine with concentrated hydrochloric
acid:

O
C
Hydrolysis of Acetamide, H3C NH2

Solution pH Reading Odor Noted

1. Acid

2. Base

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Questions

1. Effective mosquito repellents contain DEET (N,N–diethyl–3–methylbenzamide). If you

were to synthesize this compound, what carboxylic acid and amine would you begin with?
O

DEET

2. Metadone, a narcotic analgesic shown below, is dispensed as its hydrochloride salt. Explain
the usefulness of the salt rather than the amine.
N

O
Metadone

3. Nicotine is an alkaloid, meaning base-like. What structural feature is present in the

molecule that would make it react as a base?

N
Nicotine

4. Write the equations that account for what happens in the hydrolysis of the acetamide
solution in (A) acid and in (B) base. See the data sheet for the structure of acetamide.

A.

B.

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Experiment 14 – Synthesis & Characterization of

Acetylsalicylic Acid
Discussion

One of the simpler organic reactions that can be carried out is the formation of an ester from
an acid and an alcohol. This reaction proceeds as follows:

In the equation, R and R’ are H atoms or organic fragments like CH3, C2H5, or more complex
aromatic groups. There are many known esters in organic chemistry that can be synthesized
from organic acids and alcohols. The driving force for the reaction is in general not very great,
resulting in an equilibrium mixture of the formed ester, water, acid, and alcohol.

There are some esters which are solids because of their high molecular weight or other
properties. Most of these esters are not soluble in water, so they can be separated from the
mixture by crystallization. This experiment involves an ester of this type, a substance
commonly called aspirin (or acetylsalicylic acid). Aspirin is the active component in headache
pills and is one of the most effective, relatively nontoxic, pain killers.

Aspirin can be made by the reaction of the hydroxyl group (–OH group) in the salicylic acid
molecule with the carboxylic acid group (–COOH group) in acetic acid. The reaction proceeds
as follows:

A better preparative method, which we will use in this experiment, employs acetic anhydride
in the reaction instead of acetic acid. The anhydride can be considered to be the product of a
reaction in which two acetic acid molecules combine, with the elimination of a molecule of
water. The anhydride will react with the water produced in the esterification reaction and will
tend to drive the reaction to the right. A catalyst, normally sulfuric or phosphoric acid, is also
used to speed up the reaction. The reaction occurs as follows:

OH OH
O O
O O O
+ H3PO4 +
H3C O CH3 O
HO H3C H3C OH
O
acetic anhydride salicylic acid aspirin acetic acid

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The aspirin you will prepare in this experiment is somewhat impure and should certainly not
be taken internally, even if the experiment gives you a bad headache. We will attempt to purify
the aspirin via recrystallization with ethanol. If any salicylic acid remains unreacted, its
presence can be detected with a 1% iron(III) chloride solution. Salicylic acid has a phenol
group in the molecule. The iron(III) chloride gives a violet color with any molecule possessing
a phenol group. Notice the aspirin no longer has the phenol group. Thus, a pure sample of
aspirin will not give a purple color with 1% iron(III) chloride solution.

Wear gloves and safety goggles! Both phosphoric acid and acetic anhydride are corrosive!
They will burn skin! Salicylic acid is also a skin irritant.

Procedure

Prepare a 250 mL beaker of approximately 1/4 full of water. Place it on a hot plate and heat to
80 ºC. Weigh out approximately 500 mg salicylic acid in a 25 mL Erlenmeyer flask. Perform
the next operation in the fume hood: pipet 1.0 mL of acetic anhydride and pour it into the flask
in such a way as to wash any crystals of salicylic acid on the walls down to the bottom. Add 5
drops of 85% phosphoric acid to the mixture to serve as a catalyst.

Clamp the flask in the water bath, and immerse it in the hot water bath for 10 minutes, stirring
the liquid in the flask occasionally with a stirring rod. Once the reaction is complete, remove
the flask from the water bath, and CAUTIOUSLY add 10 – 20 drops of water to the mixture
to destroy any excess acetic anhydride. There will be some hot acetic acid vapor evolved as a
result of the decomposition of any unreacted acetic anhydride.

Let the flask cool for a few minutes in air, during which time crystals of aspirin should begin
to form. Put the flask in an ice bath to hasten crystallization and increase the yield of product.
If crystals are slow to appear, it may be helpful to scratch the inside of the flask with a glass
rod. Collect the aspirin by vacuum filtration. Pour distilled water over the crystals; repeat the
washing process, and then draw air through the funnel for a few minutes to help dry the
crystals. Determine the mass of your impure aspirin.

To purify your synthesized aspirin, transfer it to a 10 mL beaker and add 2 mL of ethyl alcohol
using a plastic pipet. Warm the solution to 60 ºC. Cover the solution and allow it to cool
undisturbed to room temperature. Then set the beaker in an ice bath and once again scratch the
inside of the flask with a glass rod to induce recrystallization. Collect the purified aspirin by
vacuum filtration, and let the crystals dry for a few minutes before weighing them. Determine
the mass of your dry purified aspirin.

Finally, we will test the purity of your synthesized aspirin with 1% iron(III) chloride solution
and compare with a commercial aspirin and salicylic acid. Label three test tubes; place a few
crystals of salicylic acid into test tube no. 1, a small sample of your aspirin into test tube no. 2,
and a small sample of a crushed commercial aspirin into test tube no. 3. Add 5 mL of DI water
to each test tube and swirl to dissolve the crystals. Add 10 drops of 1% aqueous iron(III)
chloride to each test tube. Record your results. The formation of a purple color indicates the
presence of salicylic acid. The intensity of the color qualitatively tells how much salicylic acid
is present.

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Data and Calculations for Experiment 14

Weight of salicylic acid added _________________________________

Volume of acetic anhydride _________________________________

Density of acetic anhydride from CRC _________________________________

Molecular Weight of acetic anhydride _________________________________

Molecular Weight of salicylic acid _________________________________

Theoretical Yield of aspirin _________________________________

Actual Yield of crude aspirin _________________________________

Actual Yield of recrystallized aspirin _________________________________

Percent Yield of recrystallized aspirin _________________________________

Test Tube No. Sample Color Intensity

1 Salicylic acid
Your synthesized
2
aspirin
Commercial aspirin
3

Questions

1. Determine the percentage yield of your crude product.

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2. 2.0 grams of salicylic acid and 5.0 mL of acetic anhydride (density = 1.08 g/mL) are mixed
to produce aspirin. Determine the percentage yield of the reaction if 1.9 g of aspirin is
actually obtained in this experiment.

3. In your own words, write a one-half page, well-written abstract of the entire experiment,
making sure to briefly state the overall purpose or goal as well as any conclusions. (For
additional guidelines on writing this abstract, please refer to the Moorpark College
Chemistry Department Laboratory Report Rubric found in the lab manual and
department website.)

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Experiment 15 – Carbohydrates

Discussion

Carbohydrates are a major food source. Rice, potatoes, bread, corn, candy, and fruits are rich
in carbohydrates. A carbohydrate can be classified as a monosaccharide (for example, glucose
or fructose), a disaccharide (sucrose or lactose), which consists of two joined monosaccharides,
or a polysaccharide (starch or cellulose), which consists of thousands of monosaccharide units
linked together. If you look at the functional groups present, carbohydrates are polyhydroxy
aldehydes or ketones or compounds that yield polyhydroxy aldehydes or ketones upon
hydrolysis (i.e., recall in biochemistry, we refer to these as aldoses and ketoses, respectively).
Monosaccharides exist mostly as cyclic structures containing hemiacetal (or hemiketal)
groups. These structures are in equilibrium in solutions with the corresponding open–chain
structures bearing aldehyde or ketone groups. Glucose, blood sugar, is an example of a
polyhydroxy aldehyde as shown below:

CH2OH CH2OH CH2OH

O OH O O OH
OH OH OH
OH H
OH OH OH
(a) (b)
OH OH OH

Disaccharides and polysaccharides exist as cyclic structures containing functional groups such
as hydroxyl groups, acetal (or ketal) groups, and hemiacetal (or hemiketal) groups. Most of the
di-, oligo-, and polysaccharides have two distinct ends. The end that has a hemiacetal (or
hemiketal) on its terminal is called the reducing end, and the one that does not contain a
hemiacetal (or hemiketal) terminal is the nonreducing end. The name “reducing” is given
because hemiacetals (and to a lesser extent hemiketals) can reduce an oxidizing agent such as
Fehling’s reagent. Consider the following disaccharide:

nonreducing end reducing end

CH2OH CH2OH
O O
OH OH
O
OH OH
OH OH

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Please note that not all disaccharides or polysaccharides contain a reducing end. An example
is sucrose (shown below), which does not have a hemiacetal (or hemiketal) group on either of
its ends:
CH2OH
O
OH
OH
OH
CH2OH O
O
HO
CH2OH
OH

Polysaccharides, such as amylose or amylopectin, do have a hemiacetal group on one of their

terminal ends, but they are mainly nonreducing substances because there is only one reducing
group present for every 2,000–10,000 monosaccharidic units. In such a low concentration, the
reducing group does NOT give a positive test with Benedict’s or Fehling’s reagent.

On the other hand, when a nonreducing disaccharide (sucrose) or a polysaccharide such as

amylose is hydrolyzed, the glycosidic linkages (acetal) are broken and reducing ends are
created. Hydrolyzed sucrose (a mixture of D–glucose and D–fructose) will give a positive test
with Benedict’s or Fehling’s reagent as well as hydrolyzed amylose (a mixture of glucose and
glucose–containing oligosaccharides). The hydrolysis of sucrose or amylose can be achieved
by using a strong acid such as HCl or with the aid of biological catalysts (i.e., enzymes).

Starch can form an intense, brilliant, dark blue or violet colored complex with iodine. The
straight chain component of starch (or amylose) gives a blue color, while the branched
component (or amylopectin) yields a purple color. In the presence of iodine, amylose forms
helixes, where the iodine molecules assemble as long polyiodide chains. The helix–forming
branches of amylopectin are much shorter than those of amylose. Therefore, the polyiodide
chains are also much shorter in the amylopectin–iodine complex than in the amylose–iodine
complex. The result is a different color (purple). When starch is hydrolyzed and broken down
to small carbohydrate units, the iodine will not give a dark blue (or purple) color. The iodine
test is used in this experiment to indicate the completion of the hydrolysis.

In this experiment you will investigate some chemical properties of carbohydrates in terms of
their functional groups.

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Reducing and Nonreducing Properties of Carbohydrates

1. Aldoses (polyhydroxy aldehydes). All aldoses are reducing sugars because they contain free
aldehyde functional groups. The aldehydes are oxidized by mild oxidizing agents (e.g.,
Benedict’s or Fehling’s reagent) to the corresponding carboxylates. For example:

NaOH
R–CHO + 2Cu+2 → R–COO–Na+ + Cu2O(s)
(from Fehling’s reagent) (red precipitate)

2. Ketoses (polyhydroxy ketones). All ketoses are reducing sugars because they have a ketone
functional group next to an alcohol functional group.

3. Hemiacetal functional group (potential aldehydes). Carbohydrates with hemiacetal

functional groups can reduce mild oxidizing agents such as Fehling’s reagent because
hemiacetals can easily form aldehydes through mutarotation.

Hydrolysis of Acetal Groups

Disaccharides and polysaccharides can be converted into monosaccharides by hydrolysis. For

example:

catalyst
Lactose + H2O → D-galactose + D-glucose

Procedure

Reducing or Nonreducing Carbohydrates

1. Place approximately 2 mL (approximately 40 drops) of Fehling’s solution (20 drops each

of solution part A and solution part B) into each of five labeled test tubes.
2. Add 10 drops of each of the following carbohydrates to the corresponding test tubes as
shown in the following table.

Test Tube No Name of Carbohydrate

1 Glucose
2 Fructose
3 Sucrose
4 Lactose
5 Starch

3. Place the test tubes in a boiling water bath for 5 min. A 600 mL (or any available large)
beaker containing about 200 mL of tap water and a few boiling stones is used as the bath.

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Record your results on your data sheet. Which of those carbohydrates are reducing
carbohydrates? Caution: Remember to use boiling stones; they prevent bumping. Handle
the hot test tubes with a test tube holder and the hot beaker with beaker tongs.

Hydrolysis of Carbohydrates

Hydrolysis of Sucrose (Acid versus Base)

1. Place 3 mL of 2% sucrose solution in each of two labeled test tubes. To the first test tube
(#1), add 3 mL of water and 3 drops of dilute sulfuric acid solution (3 M H2SO4). To the
second test tube (#2), add 3 mL of water and 3 drops of dilute sodium hydroxide solution
(3 M NaOH). Caution: To avoid burns from the acid or the base, use gloves when
dispensing these reagents.
2. Heat the test tubes in a boiling water bath for about 5 min. Then allow both solutions to
cool to room temperature by carefully placing in a test tube rack.
3. To the contents of test tube #1, add dilute sodium hydroxide solution (3 M NaOH) (about
ten drops) until red litmus paper turns blue. When using litmus paper, do NOT place the
litmus into your solution; instead, use your glass stirring rod, dipped into the test tube
solution, to spot the litmus.
4. Test a few drops of each of the two solutions (test tubes #1 and #2) with Fehling’s reagent
following the procedure that is described for carbohydrates above. Record your results on
your data sheet.

Acid–Catalyzed Hydrolysis of Starch

1. Place 5.0 mL of starch solution in a 150 x 15 – mm test tube and add 1.0 mL of dilute
sulfuric acid (3 M H2SO4). Mix it by gently shaking the test tube. Heat the solution in a
boiling water bath for about 5 min.
2. Using a clean medicine dropper, transfer about 3 drops of the starch solution into a white
spot plate and then add 2 drops of iodine solution. Observe the color of the solution. If the
solution gives a positive test with iodine solution (the solution should turn blue), the
hydrolysis is not complete and you should continue heating.
3. Transfer about 3 drops of the boiling solution at 5 min. intervals for an iodine test (Note:
Rinse the medicine dropper very thoroughly before each test). When the solution no longer
gives the characteristic blue color with iodine solution, stop heating and record the time
needed for the completion of hydrolysis on the data sheet.

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Data and Calculations for Experiment 15

Reducing or Nonreducing Carbohydrates

Test Tube Reducing or Nonreducing

Substance Color Observation Carbohydrates
No.
1 Glucose

2 Fructose

3 Sucrose

4 Lactose

5 Starch

Hydrolysis of Carbohydrates

Hydrolysis of Sucrose (Acid versus Base Catalysis)

Condition of Fehling’s Test
Sample Color Observation
Hydrolysis (positive or negative)
1 Acidic (H2SO4)

2 Basic (NaOH)

Acid-Catalyzed Hydrolysis of Starch

Heating Time Iodine Test
Sample Color Observation
(min) (positive or negative)
1 5

2 10

3 15

4 20

5 25

6 30

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Questions

1. How does the iodine test distinguish between amylose and amylopectin?

2. Why is sucrose a nonreducing sugar? Identify the glycosidic linkage present.

3. How can you tell when the hydrolysis of starch is complete? Why does the test work this
way? What is the monosaccharide that results at the end?

4. Why does amylose give a negative test with Fehling’s solution?

5. In your own words, write a logical, coherent conclusion on the back of this page which
demonstrates a thorough working knowledge and understanding of important concepts and
underlying chemical principles pertinent to this experiment, forms appropriate conclusions
based on interpretations of results, includes applications of and improvements in the
experiment, and demonstrates accountability by providing justification for any errors. If
additional space is needed, please use additional paper. (For additional guidelines on
writing this conclusion, please refer to the Moorpark College Chemistry Department
Laboratory Report Rubric found in the lab manual and department website.)

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Experiment 16 – Analysis of Lipids

Discussion

Lipids are chemically heterogeneous mixtures. The only common property they have is their
insolubility in water. We can test for the presence of various lipids by analyzing their chemical
constituents. Foods contain a variety of lipids; most important among them are fats, complex
lipids, and steroids. Fats are triglycerides, esters of fatty acids and glycerol. Complex lipids
also contain fatty acids, but their alcohol may be either glycerol or sphingosine. They also
contain other constituents such as phosphate, choline, ethanolamine, or mono– to
oligosaccharides. An important representative of this group is lecithin, a glycerophospholipid,
containing fatty acids, glycerol, phosphate, and choline. The most important steroid in food is
cholesterol. Different foods contain different proportions of these three groups of lipids.

Structurally, cholesterol contains the steroid nucleus that is the common core of all steroids:

HO
Steroid nucleus Cholesterol
There is a special colorimetric test, the Lieberman–Burchard reaction, which uses acetic
anhydride and sulfuric acid as reagents, that gives a characteristic green color in the presence
of cholesterol. This color is due to the –OH group of cholesterol and the unsaturation found in
the adjacent fused ring. The color change is gradual: first it appears as a pink coloration,
changing later to lilac, and finally to deep green.

A test that differentiates between cholesterol and lecithin is the acrolein reaction. When lipids
containing glycerol are heated in the presence of potassium hydrogen sulfate, the glycerol is
dehydrated, forming acrolein, which has an unpleasant odor. Further heating results in
polymerization of acrolein, which is indicated by the slight blackening of the reaction mixture.
Both the pungent smell and the black color indicate the presence of glycerol and therefore fat
and/or lecithin. Cholesterol gives a negative acrolein test.

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Procedure

The Acrolein Test for Glycerol

1. Place 1 g of potassium hydrogen sulfate, KHSO4, in each of seven clean and dry test tubes
(100 x 13 mm). Label them 1 through 7. To the first test tube, add a few grains of pure
lecithin; to test tube #2, add a few grains of cholesterol. To test tubes #3 - #6, add one
separate drop (which measures approximately 0.1 g) of glycerol (to #3), corn oil (to #4),
butter (to #5), and egg yolk (to #6). To the seventh test tube, add a few crystals of sucrose.
2. Set up your Bunsen burner near a hood. Caution: Perform this test near the hood due to the
pungent odor of the acrolein. When asked to smell the test tubes, do not inhale the fumes
directly. Smell the test tubes by moving them sideways under your nose or by wafting the
vapors toward your nose with a cupped hand.
3. Gently heat each test tube, one at a time, over a Bunsen burner flame, shaking it
continuously from side to side. When the mixture melts and slightly blackens, you will
notice the evolution of fumes. Stop the heating. Carefully smell the test tubes; pay attention
to the Caution above. A pungent odor, resembling burnt hamburgers, is a positive test for
glycerol. Sucrose in the seventh test tube will also be dehydrated and give a black color.
However, its smell is different and thus is not a positive test for acrolein. Do not overheat
the test tubes, for the residue will become hard, making it difficult to clean the test tubes.
Record your observations on your data sheet.

Lieberman–Burchard Test for Cholesterol

1. Take six clean and dry test tubes (150 x 18 mm). Label them 1 through 6. Place a few
grains of your cholesterol and lecithin (separately) in the first two test tubes. Similarly, add
about 0.1 g samples of glycerol, corn oil, butter, and egg yolk (separately) to the other four
test tubes.
2. Transfer 3 mL of chloroform and 1 mL of acetic anhydride to each test tube. Finally,
carefully add 1 drop of concentrated sulfuric acid to each mixture. Mix the contents and
record the color changes, if any. Wait 5 min. Record again the color of your solutions.
Record your observations on your data sheet.

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Data and Calculations for Experiment 16

Test Cholesterol Lecithin Glycerol Corn Oil Butter Egg Yolk Sucrose
A. Acrolein
a. Odor

b. Color

c. Conclusions

B. Lieberman–Burchard
a. Initial color

b. Color after 5 min

c. Conclusions

Questions

1. From your results, what is present in corn oil? Is it a pure triglyceride?

2. Based on the intensity of the color in your test for cholesterol, which food showed the
most cholesterol present? Which food showed the least cholesterol present?

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3. Consider the steroid structures shown below. Would any of these structures give a
positive Lieberman-Burchard test? Briefly explain.
O
OH OH

O O HO

Progesterone Testosterone Estradiol

4. Cholesterol is an alcohol that can dehydrate to form a carbon-carbon double bond. Draw
the structure cholesterol forms upon dehydration. Would this dehydration compound give
a positive Lieberman-Burchard test? Briefly explain.

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Experiment 17 – Viscosity & Secondary Structure of DNA

Discussion

In 1953, James Watson and Francis Crick proposed a three–dimensional structure of DNA that
is a cornerstone in the history of biochemistry and molecular biology. The double helix they
proposed for the secondary structure of DNA gained immediate acceptance, partly because it
explained all know facts about DNA, and partly because it provided a beautiful model for DNA
replication.

In the DNA double helix, two polynucleotide chains run in opposite directions. This means
that at each end of the double helix, there is one 5’–OH and one 3’–OH terminal. The sugar
phosphate backbone is on the outside, and the bases point inward. The bases are paired so that
for each adenine (A) on one chain, a thymine (T) is aligned opposite it on the other chain. Each
cytosine (C) on one chain has a guanine (G) aligned with it on the other chain. The AT and GC
base pairs form hydrogen bonds with each other. The AT pair has two hydrogen bonds; the
GC pair has three hydrogen bonds.

Most of the DNA in nature has the double helical secondary structure. The hydrogen bonds
between the base pairs provide the stability of the double helix. Under certain conditions, the
hydrogen bonds are broken. During the replication process itself, this happens, and parts of the
double helix unfold. Under separate conditions, the whole molecule unfolds, becomes single
stranded, and assumes a random coil conformation. This can happen in denaturation processes
aided by heat, extreme acidic or basic conditions, etc. Such a transformation is often referred
to as helix–to–coil transition. There are a number of techniques that can monitor such a
transition. One of the most sensitive is the measurement of viscosity of DNA solutions.

Viscosity is the resistance to flow of a liquid. Honey has a high viscosity and gasoline a low
viscosity at room temperature. In a liquid flow, the molecules must slide past each other. The
resistance to flow comes from the interaction between the molecules as they slide past each
other. The stronger this interaction, the greater the resistance and the higher the viscosity.

Spherical
Needle-Shaped (Ellipsoid)

Figure 1: Surface area of interaction between molecules of different shapes

Even more than the nature of the intermolecular interaction, the size and the shape of the
molecules influence their viscosity. A large molecule has greater surface over which it interacts
with other molecules than does a small molecule. Therefore, its viscosity is greater than that
of a small molecule. If two molecules have the same size and the same interaction forces but
have different shapes, their viscosity will be different. For example, needle–shaped molecules,

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when aligned parallel by the flow of liquid, have greater surfaces of interaction than spherical
molecules of the same molecular weight (see Figure 1). The needle–shaped molecule will have
a higher viscosity than the spherical molecule. The DNA double helix is a rigid structure held
together by hydrogen bonds. Its long axis along the helix exceeds by far its short axis
perpendicular to it. Thus, the DNA double helix has large surface area and consequently high
viscosity. When the hydrogen bonds are broken and the DNA molecule becomes single
stranded, it assumes a random coil shape, which has much lower surface area and lower
viscosity. Thus a helix–to–coil transition is accompanied by a drop in viscosity.

In practice, we can measure viscosity by the efflux time of a liquid in a viscometer (your
instructor will demonstrate in lecture). PLEASE BE CAREFUL WHEN USING THESE
VISCOMETERS; THEY ARE VERY DELICATE AND EXPENSIVE. The capillary viscometer
is made of two bulbs connected by a tube in which the liquid must flow through a capillary
tube. The capillary tube provides a laminary flow, in which concentric layers of the liquid slide
past each other. Originally, the liquid is placed in the storage bulb. By applying suction above
the capillary, the liquid is sucked up past the upper calibration mark. With a stopwatch in hand,
the suction is released, and the liquid is allowed to flow under the force of gravity. The timing
starts when the meniscus of the liquid hits the upper calibration mark. The timing ends when
the meniscus of the liquid hits the lower calibration mark of the viscometer. The time elapsed
between these two marks is the efflux time.

With dilute solutions such as the DNA in this experiment, the viscosity of the solution is
compared to the viscosity of the solvent. The efflux time of the solvent (aqueous buffer) is t o,
and that of the solutions is ts. The relative viscosity of the solution is:

rel = ts/to

The viscosity of a solution also depends on the concentration; the higher the concentration, the
higher the viscosity. In order to make the measurement independent of concentration, a new
viscometric parameter is used, which is called intrinsic viscosity, []. This number is
calculated by:

[] = (log rel) / c

which is almost a constant for a particular solute (DNA in our case) in very dilute solutions.
Please note that c represent the concentration of the DNA solution; log represents the logarithm
mathematical function as discussed earlier in lecture.

In this experiment, we follow the change in the viscosity of a DNA solution when we change
the pH of the solution from the very acidic (pH 2.0) to very basic (pH 12.0). At extreme pH
values, we expect that the hydrogen bonds will break, and the double helix will become single–
stranded random coils. A change in the viscosity will tell at what pH this happens. We shall
also determine whether two acid–denatured single stranded DNA molecules can refold
themselves into a double helix when we neutralize the denaturing acid.

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Procedure

Because of the limited number and cost of the viscometers, students may work in groups of
5 – 6. Each group will need two viscometers.

Viscosity of DNA Solutions

1. To 3 mL of a buffer solution, add 1 drop of 1.0 M HCl using a Pasteur pipet. Measure its
pH with a universal pH paper. If the pH is above 2.5, add another drop of 1M HCl. Measure
the pH again. Record the pH on your data sheet (as #1).

2. Clamp one clean and dry viscometer on a stand. Pipet 3 mL of your acidified buffer solution
into bulb A of your viscometer. Using a suction bulb of a Spectroline pipet filler, raise the
level of the liquid in the viscometer above the upper calibration mark. Release the suction
by removing the suction bulb and time the efflux time between the two calibration marks.
Record this as to on your data sheet (as #2). Remove all the liquid from your viscometer by
pouring the liquid out from the wide arm. Then apply pressure with the suction bulb on the
capillary arm of the viscometer and blow out (NOT WITH YOUR MOUTH!) any
remaining liquid into the storage bulb; pour out this residual liquid.

3. Take 3 mL of the prepared DNA solution. Add the same amount of 1 M HCl as above (1
or 2 drops). Mix it thoroughly by shaking the solution. Test the pH of the solution with a
universal pH paper and record the pH (as #3) and the DNA concentration of the prepared
solution on your data sheet (as #4).

4. Pour the acidified DNA solution into the wide arm of your viscometer. Using a suction
bulb, raise the level of your liquid above the upper calibration mark. Release the suction
by removing the suction bulb and measure and record the efflux time of the acidified DNA
solution on your data sheet (as #5).

5. Add the same amount (1 or 2 drops) as above of neutralizing 1M NaOH solution to the
liquid in the wide arm of your viscometer. With the suction bulb on the capillary arm, blow
a few air bubbles through the solution to mix the ingredients. Repeat the measurement of
the efflux time, and record it on your data sheet (as #6). For the next 100 min or so, repeat
the measurement of the efflux time every 20 min, and record the results on your data sheet
(as #7 – #11).

pH Dependence of the Viscosity of DNA Solutions

6. While the efflux time measurements in viscometer no.1 are repeated every 20 min, another
dry and clean viscometer will be used for establishing the pH dependence of the viscosity
of DNA solutions. First, measure the pH of the buffer solution with a universal pH paper.
Record it on your data sheet (as #12). Second, transfer 3 mL of the buffer into viscometer
no. 2 and measure its efflux time on your data sheet (as #13). Empty the viscometer as
instructed in step 2 above. Test the pH of the DNA solution with a universal pH paper (as
#14) and transfer 3 mL into the viscometer. Measure its efflux time, and record it on your
data sheet (as #15). Empty your viscometer.

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7. Repeat the procedure described in step 6, but this time, with the aid of a Pasteur pipet, add
one drop of 0.1 M HCl to the 3 mL buffer solution as well as to the 3 mL DNA solution.
Measure the pH and the efflux times of both buffer and DNA solutions and record them
(as #16 – #19) on your data sheet. Make sure that you carefully empty the viscometer after
each viscosity measurement.

8. Repeat the procedure described in step 6, but this time, add one drop of 0.1 M NaOH
solution to both the 3 mL buffer and 3 mL DNA solutions. Measure their pH and efflux
time and record them on your data sheet (as #20 – #23).

9. Repeat the procedure described in step 6, but this time, add 2 drops of 1 M NaOH to both
buffer and DNA solutions (3 mL of each solution). Measure and record their pH and efflux
times on your data sheet (as #24 – #27).

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Data and Calculations for Experiment 17

Viscosity of DNA solutions

(1) pH of acidified buffer ________________
(2) Efflux time of acidified buffer (t0) _____________ sec
(3) pH of acidified DNA solution ________________
(4) Concentration of DNA solution ________________
(5) Efflux time of acidified DNA solution _____________ sec
(6) Efflux time of neutralized DNA solution at time of neutralization _____________ sec
(7) 20 min. later _____________ sec
(8) 40 min. later _____________ sec
(9) 60 min. later _____________ sec
(10) 80 min. later _____________ sec
(11) 100 min. later _____________ sec

pH dependence of the viscosity of DNA solutions

(12) pH of neutral buffer ________________
(13) Efflux time of neutral buffer _____________ sec
(14) pH of DNA solution in neutral buffer ________________
(15) Efflux time of DNA in neutral buffer _____________ sec

After addition of 1 drop of 0.1 M HCl

(16) pH of buffer ________________
(17) Efflux time of buffer _____________ sec
(18) pH of DNA solution ________________
(19) Efflux time of DNA solution _____________ sec

After addition of 1 drop of 0.1 M NaOH

(20) pH of buffer ________________
(21) Efflux time of buffer _____________ sec
(22) pH of DNA solution ________________
(23) Efflux time of DNA solution _____________ sec

After addition of 2 drops of 1 M NaOH

(24) pH of buffer ________________
(25) Efflux time of buffer _____________ sec
(26) pH of DNA solution ________________
(27) Efflux time of DNA solution _____________ sec

Tabulate your data on the pH dependence of relative viscosity

pH rel
(3) __________________ (5) / (2) __________________
(14) __________________ (15) / (13) __________________
(18) __________________ (19) / (17) __________________
(22) __________________ (23) / (21) __________________
(26) __________________ (27) / (25) __________________

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Questions

1. Plot your tabulated data: relative viscosity on the y–axis, and pH on the x–axis.

2. At what pH values did you observe helix-to-coil transitions?

3. Now plot your data on the refolding of DNA double helix (5) – (11) using Microsoft Office
Excel®. Plot time on the x–axis (i.e., time after neutralization in min.) and the efflux times
on the y–axis (in sec.). Make sure to include this graph with your report. See Experiment
#18 for directions on using Excel®. Include the best-fitting line for the data points; please
note that this graph is NOT linear.

4. Was there any indication that, upon neutralization of the denaturing acid, the DNA did
refold into a double helix? Explain.

5. Compare the efflux time of the neutral DNA (15) to that of the denatured DNA 100 min.
after neutralization (11). What does the difference between these two efflux times tell you
regarding the refolding process?

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6. Calculate the intrinsic viscosity of your DNA at:

a. Neutral pH = 2.3 × {log [(15) / (13)]} / (4) =

b. Acidic pH = 2.3 × {log [(5) / (2)]} / (4) =

c. Basic pH = 2.3 × {log [(27) / (25)]} / (4) =

d. Neutral pH 100 min. after neutralization = 2.3 × {log [(11) / (13)]} / (4) =

7. A high intrinsic viscosity implies a double helix; a low intrinsic viscosity means a random
coil. What do you think is the shape of the DNA after acid denaturation and subsequent
neutralization? (See 6d above.) Explain your answer.

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Experiment 18 – Spectrophotometric Analysis of Blood

Glucose
Discussion

The normal concentration of glucose in the blood should lie within the range 65 – 95 mg
glucose per 100 mL blood. The units typically used in clinical analysis are mg/dL. The blood
glucose level may decrease temporarily during strenuous exercise because the glucose may not
be replenished rapidly enough from liver glycogen or by gluconeogenesis. A condition of low
blood glucose is called hypoglycemia. It is characterized by a rapid heartbeat, general
weakness, trembling, perspiration, whitening of the skin, and loss of consciousness. The loss
of consciousness is due to the deprivation of brain cells of the necessary glucose.

A condition of high blood glucose is called hyperglycemia. The digestion of carbohydrates

may result in absorption of glucose into the blood faster than glycogen can be formed by the
process of glycogenesis. As the blood glucose level increases, the body also transforms glucose
into fat and stores the fat as adipose tissue. When blood glucose levels reach 140 – 160 mg per
100 mL of blood, neither glycogen nor fat can be formed rapidly enough to decrease the
glucose level. The condition in which glucose is then excreted by the kidneys and eliminated
in the urine is called glucosuria.

Tests for the concentration of glucose in blood and urine are done in clinical laboratories.
Modern methods use automated analytical procedures that rapidly produce colored products
that can be analyzed by spectrophotometers. If a liquid is colored, it is because some
component of the liquid absorbs visible light of a certain wavelength. In a solution, the greater
the concentration of the light-absorbing substance, the more light absorbed and the greater the
intensity of the solution. The quantity of light absorbed by a substance can be measured using
a spectrophotometer. The instrument consists of: (1) a source that emits all wavelengths of
light in the visible region (wavelengths 400 to 700 nm); (2) a monochromator which selects a
given wavelength of light; (3) a sample holder for the solution being measured; and (4) a
detector which compares the intensity of incident light Io to the intensity of light after it has
passed through the sample I. When a beam of light passes through a substance, some of the
energy is often absorbed by the substance. This causes a decrease in the intensity of the
transmitted beam. The ratio I / Io is called the transmittance, T, a measure of the fraction of
light that passes through the sample holder (or cuvette) which contains the absorbing solution.
The amount of light absorbed by the solution is given by the absorbance, A, where:

A = –log (I / Io) = –log T

T = I/Io
Io I
A = -log (I/Io) = -log T

%T = 100% T
Absorbing Solution
of concentration c

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The distance, b, the light travels through the solution (in cm) and the concentration, c, of the
absorbing species are represented in the schematic above. A beam of parallel radiation with an
intensity is shown before (Io) and after (I) it has passed through a layer of solution with a
measured thickness at a certain concentration. The Beer-Lambert law is the basis for using
spectroscopy in quantitative analysis which relates absorbance (A) to the concentration of the
absorbing solution (c) and the path length of the cuvette (b). That is:

A=εbc

where ε is the molar absorptivity or the molar extinction coefficient. Each pure substance has
its own unique extinction coefficient. Note that during the experiment, the same cuvette should
be used for all measurements.

This experiment uses specifically prepared aqueous glucose solutions (rather than body fluids)
and Benedict’s solution. Glucose reacts with the Cu+2 complex ion of Benedict’s solution to
give solid Cu2O. As a result of this reaction, the concentration of the Cu+2 ion decreases. The
resulting decrease in the absorbance of the solution at the wavelength of maximum intensity
for the Cu+2 is directly proportional to the glucose concentration. You will determine the linear
relationship between absorbance (y-axis) and concentration (x-axis in units of mg glucose per
100 mL) using solutions generated by the reaction of various known concentrations of glucose
with Benedict’s solution. Using this calibration line (to be constructed using Microsoft Office
Excel®), you can then determine the concentration of a solution of glucose of unknown
concentration.

Procedure

Turn on the power switch by rotating it clockwise. The pilot light will glow red when the
machine is on. Note that the power switch is also the zero control knob (left side knob). Set the
wavelength control to 730 nm and allow the spectrophotometer to warm up for 15 minutes.
Adjust the zero control knob so that it reads 0% T.

Prior to making all absorbance readings, a spectrophotometer must be calibrated using a blank
solution, which is comprised of a cuvette filled with 2/3 full D.I. water for this experiment.
Insert the cuvette into the sample holder, aligning the mark on the test tube with the line on the
sample compartment and close the cover. Adjust the transmittance/absorbance control (right
side knob) until the meter reads 100% T.

Obtain an unknown solution sample from your instructor. Mark the unknown code on your
data sheet.

Prepare and number six test tubes, and carefully pipet 5.00 mL of the dilute Benedict’s solution
into each tube. Now obtain a different pipet for each subsequent addition: into tube 1, pipet
5.00 mL of D.I. water; into tubes 2 through 5, pipet 5.00 mL of the different standard glucose
solutions found in the hood. Into tube 6, pipet 5.00 mL of your unknown glucose solution.

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Gently agitate each test tube to ensure complete mixing. Place all tubes in a 400 mL beaker
containing 200 mL of hot water maintained at a gentle boil via a Bunsen burner with boiling
chips. After 30 minutes, remove the test tubes and place them in a test tube rack to cool. If the
Cu2O formed in the reaction settles to the bottom of the test tubes, it will be possible to decant
the solution; otherwise, you will have to centrifuge the mixture to separate the solid from the
solution before decanting.

Obtain two cuvettes from your instructor, calibrate the spectrophotometer with the blank
solution, and record your absorbance measurements for the six solutions. Make certain to rinse
the sample cuvette several times with small amounts of the new solution prior to recording its
absorbance. Record your results in the data section of this report.

Excel® Guidelines

Note that various versions of Excel® may function a bit differently from the directions outlined
below (which work on department-owned laptop computers):

Put the title for your x-axis (include units) in one Excel® cell (box). In the cell to the right, put
the title for your y-axis. Using these boxes as headings, input the numeric data (like a table) in
the cells under these titles (each box should contain one number; each row represents one data
point in x,y format). Click and drag your mouse to highlight just the numeric boxes. From the
“Insert” tab, choose a “Scatter” plot. (See example, below.)

Your graph must include a meaningful Chart Title and Axis Titles (with units). These Chart
Elements can be added to your graph by clicking on the “+” icon in the upper right corner of
your graph. Your instructor may request additional Chart Elements.

To add a Trendline, right click on any data point on your graph and choose “Display Trendline”
from the menu that appears. The format trendline pane will appear on the right side of your
screen. Linear should be selected by default. From this pane, you should check the box next to
“Display Equation on chart.” Your instructor may also ask you to check the box for “Display
R-squared value on chart.”

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Data and Calculations for Experiment 18

Initial glucose concentration Absorbance

Test Tube
(from bottle) at 730 nm
1

5
Unknown Code
To be determined in Question #1 below
__________

Based on your Excel® graph, what is the equation of the line? _________________________

Questions

1. Using your unknown absorbance value and calibration line, what is the concentration of
your unknown solution? Show your work below.

2. The following absorbance values for four solutions with known MnO4– concentrations
were measured using a spectrophotometer:

Solution [MnO4–] Absorbance

1 7.00 x 10–5 M 0.175
2 1.00 x 10–4 M 0.250
3 2.00 x 10–4 M 0.500
4 3.50 x 10–4 M 0.875

Plot a graph of Absorbance vs. Concentration of MnO4– using Microsoft Excel® (be sure
to include your graph with this report). Determine the concentration of an unknown
MnO4– sample whose absorbance is found to be 0.780.

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3. In your own words, write a logical, coherent conclusion which demonstrates a thorough
working knowledge and understanding of important concepts and underlying chemical
principles pertinent to this experiment, forms appropriate conclusions based on
interpretations of results, includes applications of and improvements in the experiment, and
demonstrates accountability by providing justification for any errors. If additional space is
needed, please use the back of this page. (For additional guidelines on writing this
conclusion, please refer to the Moorpark College Chemistry Department Laboratory
Report Rubric found in the lab manual and department website.)

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Experiment 19 – Synthesis and Characterization of Soap

In this experiment, you will prepare a soap from vegetable oil. The properties of your soap will
be compared to those of commercial soaps and detergents under various conditions.

Discussion

Common experience has shown us that oil and water do not mix. This behavior is due to the
fact that oil molecules are nonpolar, while water is very polar. In fact, oil and water repel one
another, making the removal of oil stains very difficult with water alone. To remove an oil
stain on a piece of clothing, it is necessary to add soap or detergent in order to make the oil
dissolve into the wash water. The unique chemical structure of soap allows it to act as a "go-
between" for the water and oil.

Most water-soluble soaps are sodium or potassium salts of long chain organic acids. Soaps are
prepared from natural fats or oils with strong base such as NaOH. All fats and oils have the
general structure shown below, with the R, R', and R" signifying hydrocarbon chains of varying
length. Glycerol and soap salts (e.g., sodium salts of fatty acids produced from oil and sodium
hydroxide) are the products.

Sodium stearate is a common commercial soap and has the formula NaC18H35O2. In water, this
compound dissolves to form sodium ions and stearate ions (see structure below). The stearate
ion consists of a long, nonpolar hydrocarbon chain that dissolves well in oil, and a polar,
negatively charged end that dissolves in water.

The nonpolar chain and the charged (ionic) tail are referred to as the "hydrophobic" (water-
fearing) and "hydrophilic" (water-loving) parts, respectively. When washing oil-stained
clothing, the hydrophobic tails of the soap are attracted into the oil spot. As motion of the water

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molecules tugs the charged end back and forth, the oil is pulled free from the fabric in small
droplets that become surrounded by soap ions. These spherical beads, called micelles, repel
one another due to the charged ends on the surface (see figure below) and remain dispersed
throughout the wash water. Such a dispersion is called an emulsion.

For a soap to function well as a cleaning

agent, it must be dissolved in water. In
hard water, ions such as Ca+2 and Mg+2
will precipitate with the soap anions as an
insoluble solid. Since this precipitate is
not very dense, it usually floats and is
usually visible as soap scum or bathtub
ring. As soap scum removes soap ions
from solution, cleaning in hard water is
difficult unless more soap is added to
compensate for the loss. Another
alternative is to "soften" the water by removing most of the troublesome metal ions.

Soap ions must also retain their charged ends in order to remain functional. In acidic water, the
soap anion will act as a base, accepting a hydrogen ion to form the neutral fatty acid with the
end group, COOH. Without the charged end, the soap will not be attracted as strongly to water,
will not form micelles, and thus will not remove and emulsify the oil. In some cases, the acid
form of the soap may be insoluble if sufficient polarity is lost. One solution to this problem is
to use detergent instead of soap. A detergent consists of a long hydrophobic chain with a
hydrophilic head, but the head is a less reactive [—SO3–] group instead of the [—CO2–] found
in soap. These detergent ions will remain soluble in hard and acidic water, and thus are more
effective under such conditions. Sodium lauryl sulfate, CH3(CH2)11OSO3–Na+ (abbreviated
ROSO3–Na+), is a common detergent used in shampoos. Also, some commercial soaps and
detergents contain additives such as phosphates to reduce the acidity of the water used.

Cautions

Ethanol is flammable, so no open flames are allowed. Sodium hydroxide solutions are
corrosive to skin and clothing, so avoid contact. If contact occurs, rinse with lots of water.

Procedure

1. Place 5 g of vegetable oil in a 125 mL Erlenmeyer flask. Add 5 mL of ethanol. Swirl the
solution to mix the layers together.

2. Add 7 mL of 5 M NaOH. Swirl the solution well and pour into a 100 mL beaker. Stir with
a long glass rod while heating gently (setting at 3–4) on a hot plate. Continue to heat while
stirring frequently, until the mixture is a stiff paste. This may take up to 30–40 minutes.
After the paste has formed, allow the beaker to cool for 15 minutes until slightly warm to
the touch.

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3. Add 25 mL of saturated NaCl solution to the cooled paste and stir, breaking up the large
chunks of paste by pressing them against the side of the beaker. This procedure is known
as "salting out". Be careful not to overdo the breaking up, or your soap won’t filter well.

4. Filter the soap mixture by suction filtration. (NOTE: Pour most of the liquid through first
because the soap may clog the filter.) Wash once with 10 mL of ice water through the filter,
then allow it to drain for 5 minutes with the aspirator on.

5. Make separate solutions of 1) your prepared soap; 2) a commercial soap; and

3) a commercial detergent as follows: Warm about 300 mL of D.I. water on a hot plate
until it reaches about 60 °C. Dissolve about 0.25 g of each of the test materials in 100 mL
of the warm water in 250 mL beakers. Stir well to ensure that all of the soap or detergent
has dissolved. These will serve as your test solutions for the following steps.

6. pH: Test the pH of each solution and D.I. water using universal indicator paper. For each
solution, use a clean glass rod to transfer a drop of solution to the paper. Record your
results.

7. Emulsifying properties: Label 4 clean, dry test tubes to correspond with each of your test
solutions plus D.I. water. Place 10 mL of each test solution into its labeled test tube, and
10 mL D.I. water into the fourth. Add 10 drops of paraffin oil to each test tube and shake,
and immediately after shaking, record how uniformly the oil and water are distributed
throughout the mixture. Leave the tubes undisturbed for 1 minute, then again record your
observations on how well the oil and water remain mixed, and how much oil has recollected
at the top.

8. Effect of Hard Water: Label 4 clean, dry test tubes to correspond with each of your test
solutions plus D.I. water. Place 10 mL of each test solution into its labeled test tube, and
10 mL D.I. water into the fourth. Shake each tube to observe the head of “suds” produced
(the D.I. will provide you with a comparison with no suds). Add 2 mL of "hard water"
provided (contains Ca+2 and Mg+2 ions) to the first tube, shake well, and observe any
changes, looking for cloudiness, precipitate, lack of suds, etc. Record you observations.
Allow to stand for 5 minutes and then observe again. Record any further changes. Repeat
for the remaining test solutions.

9. Cleaning Properties: Use tap water to wash your hands with some of the soap you made.
Note how well (or how poorly) it lathers. If there was an excess of oil used in making the
soap, it may leave a greasy film on your skin. If there was an excess of NaOH used in
making the soap, your hands may feel slippery during washing and rinsing, but not greasy.
Rinse your hands well and dry them. Record your observations on the lathering properties
and the “feel” of your soap. Dispose of your product in the trash.

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Data and Calculations for Experiment 19

A. pH

Solution pH

1. Prepared Soap _________

2. Commercial Soap _________

3. Commercial Detergent _________

4. D.I. Water _________

B. Emulsifying Properties

Solution Initial Observations Observations After 1 Minute

1. Prepared Soap

2. Commercial Soap

3. Commercial Detergent

4. D.I. Water

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C. Effect of Hard Water

Solution Initial Observations Observations After 5 Minutes

1. Prepared Soap

2. Commercial Soap

3. Commercial Detergent

D. Describe the washing properties of your soap in terms of lathering ability and feel.

Questions

1. Which solution was most basic according to pH measurements?

2. Which solution(s) show(s) the best ability to emulsify oil?

3. Explain your observations for the addition of hard water. What is happening in each test
tube and why?

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Experiment 20 – DNA Extraction from an Onion

In this experiment, you will extract deoxyribonucleic acid (DNA) from the cells of an onion
and will detect the presence of DNA in your sample using a qualitative test.

Discussion

DNA, a polymer found in all living cells, contains all of the genetic information needed for
controlling cellular growth and development. Errors in DNA are the basis for thousands of
genetic diseases.

In complex cells, such as those in multicellular animals and plants, DNA is found within a
membrane-bound nucleus. To isolate DNA, the cells and associated membranes must be
ruptured. A crude preparation of DNA can then be isolated from the dozens of other cellular
components.

First, cell membranes are broken by grinding them with sand in a buffered detergent solution.
The detergent weakens the cellular membranes and deactivates enzymes, called nucleases, that
would destroy the DNA. DNA is more soluble and more stable under slightly basic conditions,
so the detergent solution is buffered to pH 8.

To precipitate the DNA from the cellular solution, ethyl alcohol can be added to the extract.
The DNA prepared in this manner will not be pure because cells contain ribonucleic acid
(RNA) as well as thousands of different proteins that will precipitate under these conditions as
well. Several additional purification steps would be required if DNA needed to be separated
from these other substances.

To verify that DNA is present in the precipitate, it can be mixed with diphenylamine, which
reacts with the deoxyribose portion of DNA producing a blue color. The intensity of the blue
color is proportional to the amount of DNA in the sample.

In this experiment, you will extract DNA from onion cells using these principles and will verify
the presence of DNA using the diphenylamine test.

Procedure

As you complete this experiment, record your observations on the Data and Observations sheet.

1. Obtain a chilled mortar and pestle.

2. Obtain approximately 5 grams of onion. Cut the onion into small pieces with a knife and
place these into the cold mortar.

3. To the mortar, add an amount of sand similar in size to your portion of onion.

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4. Obtain 10 mL of chilled buffered detergent solution and pour this into the mortar with the
onion and sand.

5. Grind the onion-sand mixture for at least 5 minutes and record your observations.

6. Obtain a funnel, a ring support, a support stand, a piece of cheesecloth, and a 30-mL beaker.
Assemble the filter assembly shown in figure 1. Fold the cheesecloth to make four layers
large enough to cover the funnel and line the funnel with the folded cheesecloth.

Figure 1: Filtration assembly

7. Pour the slurry of ground onion and sand onto the cheesecloth. Scrape any solid pieces out
of the mortar. Lift up the cheesecloth by the edges, twist the cloth to enclose the solid
pieces of onion, and press it against the wall of the funnel to remove as much liquid as
possible. Record your observations.

8. Obtain two test tubes sized to fit your laboratory centrifuge. Label the tubes with your
initials. Transfer the onion filtrate to one of the tubes. The second test tube is the balance
tube. Fill the balance tube with water to a level that is equal to the level of the filtrate in
the first tube.

9. Place the two tubes into opposite positions in a centrifuge. NEVER operate the centrifuge
unless there are pairs of equally-filled test tubes on opposite sides to maintain balance.
Close the cover and be sure that your hands and clothing are clear from spinning parts.
Turn on the centrifuge for 5 minutes. While your sample is being centrifuged, rinse your
beaker with deionized water and allow it to drain.

10. After 5 min, turn off the centrifuge and allow it to come to a stop. Record your observations
of the supernatant (liquid portion) and the precipitate. Decant the supernatant back into the
30-mL beaker.

11. Dispose of the precipitate, the cheesecloth and the residual onion solids in the trash.

12. Into a second 30-mL beaker, pour enough cold ethyl alcohol to equal the volume of liquid
in the beaker containing the DNA solution.

Chemistry M11 Laboratory Manual Page 112

Name: _________________________________ Section: _____________________

13. Tilt the DNA beaker slightly. Carefully pour the cold ethyl alcohol down the side of the
beaker as shown in Figure 2. The ethyl alcohol should form a layer on top of the filtrate.

Figure 2: Precipitation of DNA

14. Examine the interface between the layers of ethyl alcohol and filtrate. Record your
observations. The DNA should appear as fibers at the ethyl alcohol/filtrate interface while
the gelatinous material consists mostly of proteins and RNA. Wait 2-3 minutes while you
continue to record your observations. Then, carefully pierce the interface with a glass rod
and rotate (but do NOT stir) the rod at the interface of the two layers to wind the DNA
fibers around the rod. Remove any excess liquid by pressing the rod against the inner wall
of the beaker.

15. Place your DNA onto a watch glass and record your observations about the appearance of
the DNA fibers.

16. Pour the contents of the small beaker into the appropriate waste container.

17. CAUTION: The diphenylamine reagent is toxic and contains sulfuric acid and acetic
acid, which are corrosive. It must be used in the fume hood. Prepare a boiling water bath
for use in the fume hood. Add about 125 mL of water to a 250-mL beaker and place it on
top of a hot plate. Use a ring support to prevent the beaker from tipping over (Figure 3) and
bring the water to a boil.

Figure 3: Boiling water bath set-up.

18. Transfer 2 mL of diphenylamine reagent to a small test tube. Add a small piece of your
DNA sample. Mix well. Heat in a boiling water bath for 10 min. Record your observations.

19. Dispose of your test solution and any unused DNA as directed by the instructor. Be sure
to wash your hands thoroughly with soap before leaving the laboratory.

Chemistry M11 Laboratory Manual Page 113

Name: _________________________________ Section: _____________________

Post-Lab Questions

1. Suggest several ways that the procedure might be changed to increase the amount of DNA
extracted from the onion cells.

2. Suppose a student added ethyl alcohol directly to the onion cell filtrate without first
centrifuging the sample. What do you think the student would observe? Would the student
be successful in extracting the DNA? Explain.

3. Would you expect similar results if you were to use other cells, such as beef liver or yeast
as sources of DNA? Explain your reasoning.

4. Consider a single-celled organism, such as a bacterium, whose DNA is not enclosed within
a membrane bound nucleus.

a) Would you predict that it would be easier or harder to extract the DNA from a bacterial
cell compared to extracting DNA from onion cells? Briefly explain.

b) Would you predict that a single-celled bacterial organism would have as much DNA
as a cell from a more complex organism, such as an onion? Explain.

Chemistry M11 Laboratory Manual Page 114

Name: _________________________________ Section: _____________________

Data and Observations

Record your observations from…

Step 5:

Step 7:

Step 10:

Step 14:

Step 15:

Step 18:

Chemistry M11 Laboratory Manual Page 115

Name: _________________________________ Section: _____________________

Solubility Rules
A compound is soluble in a particular liquid if it dissolves in that liquid. A compound is
insoluble if it does NOT dissolve in the liquid. There is no easy way to tell whether a
particular compound will be soluble or insoluble in water. For ionic compounds, however,
there are empirical rules that have been deduced from observations of many compounds.
Consider the following:

Compounds Containing the Following Ions

Are Mostly Soluble* Exceptions

Li+, Na+, K+, NH4+ None

NO3–, C2H3O2– None

Cl–, Br–, I– When any of these ions pairs

With Ag+, Hg2+2, Pb+2, or
Cu+, it is insoluble

SO4–2 When SO4–2 pairs with Sr+2,

Ba+2, Pb+2, or Ca+2, it is
insoluble
Compounds Containing the Following Ions
Are Mostly Insoluble* Exceptions

OH–, S–2 When either of these ions

pairs with Li+, Na+, K+, or
NH4+, it is soluble

S–2 When S–2 pairs with Sr+2,

Ba+2, or Ca+2, the compound
is soluble

OH– When OH– pairs with Sr+2,

Ba+2, or Ca+2, it is slightly
soluble**

CO3–2, PO4–3 When either of these ions

pairs with Li+, Na+, K+, or
NH4+, it is soluble
*adapted from Tro, Nivaldo J. Introductory Chemistry, 2nd ed. Upper Saddle River:
Prentice Hall, 2006.

** For our purposes, these can be considered insoluble

Chemistry M11 Laboratory Manual Page 116

Name: _________________________________ Section: _____________________

Names, Formulas, and Charges of Common Polyatomic Ions

Positive Ion (Cation)

1+ Ammonium NH4+

Negative Ions (Anions)

1– Acetate C2H3O2–
Bromate BrO3–
Chlorate ClO3–
Chlorite ClO2–
Cyanide CN–
Hydride H–
Hydrogen Carbonate (bicarbonate) HCO3–
Hydrogen Sulfate (bisulfate) HSO4–
Hydroxide OH–
Hypochlorite ClO–
Iodate IO3–
Nitrate NO3–
Nitrite NO2–
Perchlorate ClO4–
Permanganate MnO4–
Thiocyanate SCN–
2– Carbonate CO32–
Chromate CrO42–
Dichromate Cr2O72–
Oxalate C2O42–
Peroxide O22–
Sulfate SO42–
Sulfite SO32–
3– Arsenate AsO43–
Phosphate PO43–
Phosphite PO33–

Chemistry M11 Laboratory Manual Page 117

 Moorpark College Chemistry Department Laboratory Report Rubric
Name: ______________________________ Experiment: ____________________________ Total: _______
CATEGORY 4 – Accomplished 3 – Good 2 – Developing 1 – Beginning 0 – Substandard Score
Clear, concise (~½ page), Refers to most of the Misses one or more Missing several major None, unrelated, or
and thorough summary of major results; some minor major aspects of the aspects of the results and plagiarized.
Abstract results with appropriate details are missing or not results. merely repeats information
_____×2
literature references. clearly stated. from the introduction.
A cohesive, well-written Introduction is nearly Certain major Very little background None, unrelated,
summary (including complete but does not introductory points are information is provided, or plagiarized.
relevant reaction chemistry) provide context for minor missing (e.g., and information is
of the background material points. Contains relevant background, theory, incorrect. No references
pertinent to the experiment information but fails to reaction chemistry), or are provided.
Introduction with appropriate literature provide background for explanations are unclear
_____×2

Chemistry M11A Laboratory Manual

references (at least one one aspect of the and confusing.
scientific reference if experiment, or certain References are not
required by your instructor) information is not scholarly.
and a statement of purpose. cohesive.
Contains a complete listing Narrative includes most Narrative is missing Several important None, unrelated, or
of safety information, a important experimental several experimental experimental details and plagiarized
narrative of experimental details. Missing one or details and safety safety information are (including
procedures followed, and more relevant pieces of information or includes missing. Procedural steps completely copied
Methods materials used. Omits safety information or insignificant procedural are incorrect, illogical, or from the laboratory
& information that can be experimental procedure. details. occasionally copied manual). _____
Materials assumed by peers. Includes directly from the
observations when laboratory manual.
appropriate and only
important experimental
details.
All figures, graphs, and All figures, graphs, and Most figures, graphs, and Figures, graphs, and tables None, unrelated, or
tables are numbered with tables are correctly drawn, tables are included, but are poorly constructed, plagiarized.
appropriate titles and but some have minor some important or have missing titles,
Results
captions. Sample problems or could still be required features are captions or numbers.
& calculations are shown and improved. All data and missing. Certain data and Certain data and sample
_____×2
Calculations correctly solved. All data is sample calculations are sample calculations are calculations are not
explicitly mentioned in the mentioned in the text. not explained in the text referenced in the text and
text. and/or solved incorrectly. solved incorrectly.

Page 118
 CATEGORY 4 – Accomplished 3 – Good 2 – Developing 1 – Beginning 0 – Substandard Score
Demonstrates a logical, Demonstrates an While some of the Does not demonstrate None, unrelated,
coherent working knowledge understanding of the results have been an understanding of insignificant error
and understanding of majority of important correctly interpreted the important analysis and
important experimental experimental concepts, and discussed, partial experimental incorrect
concepts, forms appropriate forms conclusions based but incomplete concepts, forms explanation, or
conclusions based on on results and/or understanding of inaccurate plagiarized.
interpretations of results spectrum (spectra) results is still evident. conclusions, does not
and/or spectrum (spectra) analysis but either lacks Student fails to make answer post-lab
Discussion
analysis, addresses any post- proper interpretation, one or two questions in
& lab questions in paragraph does not answer post-lab connections to paragraph format,
_____×2
Conclusion format, includes applications questions in paragraph underlying theory. suggests
of and improvements in the format, suggests inappropriate
experiment, refers to the inappropriate improvements in the
literature when appropriate, improvements in the experiment, refers to

Chemistry M11A Laboratory Manual

and demonstrates experiment, refers to the the literature
accountability by providing literature insufficiently, insufficiently, and
justification for any errors. or lacks overall lacks overall
justification of error. justification of error.
All sources (information and All sources are All sources are All sources are Sources are not
graphics) are accurately accurately documented, accurately accurately documented nor
documented in ACS format. but a few are not in ACS documented, but documented but not directly cited in the
References* At least one reference is taken format. Some sources are many are not in ACS directly cited in the text. _____
(see sample below)
from primary scientific not accurately format. Most sources text.
literature relevant to the report documented. are not directly cited
if required by instructor. in the text.
Miscellaneous Grammar and spelling are Less than three More than three Frequent grammatical None, unrelated, or
(check all that apply) correct. All required grammatical and spelling grammatical and and spelling errors, plagiarized.
components are included, errors are present. spelling errors are and writing style
 Mechanics, grammar, complete, and/or illustrated Missing one required present or paper is lacks cohesion and
and appearance correctly. Paper is not written component or features an written in first fluidity. Paper is
_____×2
 Appendix in first person. Includes improperly labeled person. Features written in first
 Lab Notebook ChemSketch image(s) if molecular representation. multiple errors with person. Labeled
 VSEPR and Valence required by instructor. For labeled molecular molecule contains
Bond drawings Chem 1A XY lab, see lab representation. multiple errors.
manual for more details.
*Journal citations must include author or editor, title (in italics) followed by a period, year (boldface), volume (in italics), and page numbers. For example:
Schrauzer, G.N.; Windgassen, R.J. J. Am. Chem. Soc. 1966, 99, 3738-3743. For additional examples, see the ACS Style Guide (summary can be found online).

Page 119
 Periodic Table of the Elements

IA VIII A
1 18
1 2
H II A III A IV A VA VI A VII A He
1.008 2 13 14 15 16 17 4.003
3 4 5 6 7 8 9 10
Li Be B C N O F Ne
6.941 9.012 10.811 12.011 14.007 15.999 18.998 20.180
11 12 13 14 15 16 17 18
Na Mg III B IV B VB VI B VII B ---- VIII B ---- IB II B Al Si P S Cl Ar

Chemistry M11A Laboratory Manual

22.990 24.305 3 4 5 6 7 8 9 10 11 12 26.982 28.086 30.974 32.066 35.453 39.948
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
39.098 40.078 44.956 47.88 50.942 51.996 54.938 55.847 58.933 58.693 63.546 65.39 69.723 72.61 74.922 78.96 79.904 83.80
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
85.468 87.62 88.906 91.22 92.906 95.94 (98) 101.07 102.91 106.42 107.87 112.41 114.82 118.71 121.76 127.60 126.90 131.29
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
132.91 137.33 138.91 178.49 180.95 183.84 186.21 190.23 192.22 195.08 196.97 200.59 204.38 207.2 208.98 (209) (210) (222)
87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
(223) 226.03 227.03 (261) (262) (266) (264) (277) (268) (281) (272) (285) (284) (289) (288) (293) (294) (294)

58 59 60 61 62 63 64 65 66 67 68 69 70 71
Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
140.12 140.91 144.24 (145) 150.36 151.96 157.25 158.92 162.50 164.93 167.26 168.93 173.04 174.97
90 91 92 93 94 95 96 97 98 99 100 101 102 103
Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
232.04 231.04 238.03 237.05 (244) (243) (247) (247) (251) (252) (257) (258) (259) (260)

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