I.

THEORETICAL BACKGROUND

Organic compounds called alcohols have a hydroxyl (-OH) group in them. Molecules
with a -OH group directly linked to a benzene ring are known as phenols. Alcohols fall into one
of three categories: primary, secondary, or tertiary. Whether the alcohol carbon is joined to one,
two, or three alkyl groups determines how this classification is made. The various kinds of
alcohol react differently, hence this classification is significant (Farmer, et.al., 2016).

McMurray (2017) stated that an alcohol has the general formula ROH, where R is an
aliphatic hydrocarbon group. Alcohols can be thought of as HOH-derivatives of water. An alkyl
group, R, replaces one of the hydrogen atoms in water. Alcohols exhibit hydrogen bonding, just
like water. The polarity of the molecule is overshadowed by its hydrocarbon property as the chain
of the R group lengthens the personality of the OH group.

In reactions involving alcohol, it can serve as both an electrophile and a nucleophile.

Alcohols function as nucleophiles in processes in which the bond between O and H is broken.
Alcohols can behave as electrophiles in processes when the bond between C and O is broken.
While phenols are particularly reactive due to an ortho-para director function performed by an
attached hydroxyl group to an aromatic ring. As a result, electrophilic aromatic substitution is
strongly attracted to the ortho and para carbons of phenol according to Soderburg (2015).

II. TLO
TLO#12:
- To observe and determine the classification of alcohols.
- To examine physical and chemical properties of representative alcohols and phenols. 
- To compare the chemical behavior between these compounds.
- Use these observations and information to identify an unknown sample.

III. PROCEDURES
NOTE ON WASTE DISPOSAL:
Dispose any aqueous solution by diluting them and pouring them into the sink. Any remaining
organic compound should be disposed into the appropriate organic waste container.

A. Solubility in Water 
1. Put 10-drop samples of the following into separate, labeled test tubes: ethyl alcohol, isopropyl
alcohol, t-butyl alcohol, ethylene glycol, benzyl alcohol, and resorcinol.
2. To each tube, add 3 ml of distilled water, mix thoroughly. Record your observations.

B. Lucas Test 
1. Put 5-drop samples of the following into separate, labeled test tubes: ethyl alcohol, isopropyl
alcohol, -butyl alcohol, resorcinol.
2. Add 10 drops of Lucas reagent to each sample and mix the contents well by agitation
Safety Alert:
Lucas Reagent contains concentrated hydrochloric acid (HCI) that will vigorously damage tissue.
Contact should be avoided. If you get any on your skin, wash it off immediately with cool water
and inform your instructor.
 3. Observe the test tubes within a minute after mixing and note whether or not cloudiness has
developed. Put any tubes with clear solutions into a boiling water bath and observe again after
heating for two minutes.
4. Record your observations.

C. Oxidation (Bordwell-Welman Test) 

1. Put 5-drop samples of the following into separate, labeled test tubes: ethyl alcohol, isopropyl
alcohol, t-butyl alcohol, resorcinol.
2. Add 10 drops of reagent grade acetone to each test tube.
3. Shake each test tube to mix the contents.
4. Add 5 drops of potassium dichromate.
5. Acidify with 2 drops of concentrated sulfuric acid. (CAUTION: USE GLOVES WITH
CONCENTRATED SULFURIC ACID) Mix well.
6. Observe the test tubes after 3 minutes and record your observation.

D. IODOFORM TEST 
1. Put 10 drops of the following compounds into separate test tubes: ethyl alcohol, propyl alcohol,
isopropyl alcohol, phenol.
2. Add 20 drops of I —KI solution to each tube and mix thoroughly.
2

3. To each test tube, add 5 drops of 10% NaOH solution. Mix well. Observe for any color
changes or precipitation.
4. Record your observation in Table 12-4.

E. THE ACIDITY OF PHENOLS 

1. Place 5-drop samples each of ethyl alcohol, liquid phenol, and resorcinol into separate
test tubes.
2. Add 20 drops of distilled water to each test tube and mix thoroughly.
3. Place 20 drops of distilled water to a separate clean test tube.
4. Using wide-range pH paper, measure the pH of each solution and that of the pure water.
5. Record each pH value.

F. REACTION with FERRIC CHLORIDE 

1. Place 5-drop samples each of isopropyl alcohol, liquid phenol, and resorcinol, diluted salicylic
acid solution into separate test tubes.
2. Add 20 drops of distilled water to each test tube and mix thoroughly.
3. To each, add 2 drops of ferric chloride solution, swirl the contents, and record the results.

IV. DATA & RESULTS

(A)SOLUBILITY in WATER 
Sample Solubility in Water

Ethyl alcohol soluble

Isopropyl alcohol soluble

t-Butyl alcohol soluble

Ethylene glycol soluble

Benzyl alcohol partially soluble or almost insoluble 

 Resorcinol soluble

(B)LUCAS TEST 
Sample Appearance within 1 Minute Appearance after 2-Minutes heating
Ethyl alcohol The solution was clear, however there were No significant  reaction
several black dotted precipitates
Isopropyl The solution was clear No significant  reaction
alcohol
t-Butyl The solution became cloudy N/A
alcohol
Resorcinol The solution was clear A separating layer was present and
visible after heating

(C)OXIDATION
Sample Result of adding acidified potassium dichromate

Ethyl alcohol The solution was clear and blue green in color.

Isopropyl alcohol The solution was clear and adriatic blue in color.

t-Butyl alcohol The solution was clear and la rioja yellow in color

Resorcinol The solution was dark green in color (similar to the lagundi syrup color)

(D)IODOFORM TEST
Sample Result of adding I2 —KI solution
Ethyl alcohol It turned into a cloudy solution.
Propyl alcohol It turned into a clear solution.
Isopropyl alcohol It turned into a clear solution.
Phenol There was a separation/precipitate.

( E)ACIDITY OF PHENOLS
Sample Solution pH Acid, Base
or Neutral
Ethyl 5 Acid
alcohol

Phenol 4 Acid
 Resorcinol 3 Acid

Water The pH of pure water (H20) is 7 at 25 °C, but it was exposed to the Neutral
carbon dioxide in the atmosphere which this equilibrium resulted in a
pH of approximately 5

(F)REACTION WITH FERRIC CHLORIDE

Sample Result of adding Ferric Chloride

Isopropyl alcohol It resulted in a clear yellowish solution with precipitates.

Phenol It resulted in a clear yellowish solution with separation at the bottom.

Resorcinol It resulted in a dark violet solution with bluish tint.

Salicylic acid

A. It resulted in a darker violet solution with a few solids from the salicylic SOLUBILITY in
WATER 
Sample Solubility in Water

Ethyl alcohol soluble

Isopropyl alcohol soluble

t-Butyl alcohol soluble

Ethylene glycol soluble

Benzyl alcohol partially soluble or almost insoluble 

Resorcinol soluble

B. LUCAS TEST 
Sample Appearance within 1 Minute Appearance after 2-Minutes heating
Ethyl alcohol The solution was clear, however there were No significant  reaction
several black dotted precipitates
Isopropyl The solution was clear No significant  reaction
alcohol
t-Butyl The solution became cloudy N/A
alcohol
Resorcinol The solution was clear A separating layer was present and
visible after heating

C. OXIDATION
Sample Result of adding acidified potassium dichromate

Ethyl alcohol The solution was clear and blue green in color.

Isopropyl alcohol The solution was clear and adriatic blue in color.

t-Butyl alcohol The solution was clear and la rioja yellow in color

Resorcinol The solution was dark green in color (similar to the lagundi syrup color)

D. IODOFORM TEST
Sample Result of adding I2 —KI solution
Ethyl alcohol It turned into a cloudy solution.
Propyl alcohol It turned into a clear solution.
Isopropyl alcohol It turned into a clear solution.
Phenol There was a separation/precipitate.

E. ACIDITY OF PHENOLS
Sample Solution pH Acid, Base
or Neutral
Ethyl 5 Acid
alcohol

Phenol 4 Acid

Resorcinol 3 Acid

Water The pH of pure water (H20) is 7 at 25 °C, but it was exposed to the Neutral
carbon dioxide in the atmosphere which this equilibrium resulted in a
pH of approximately 5

F. REACTION WITH FERRIC CHLORIDE

Sample Result of adding Ferric Chloride
Isopropyl alcohol It resulted in a clear yellowish solution with precipitates.

Phenol It resulted in a clear yellowish solution with separation at theacid.

V. DISCUSSION
 VI. DISCUSSION
VII. Alcohols and phenols are organic compounds that have at least one hydroxyl group bonded to
either a saturated or aryl carbon. The hydroxyl group is connected to a vinylic carbon in
enols, a similar third family of chemicals. Moreover, A phenol is an organic molecule that
has a hydroxyl group that is directly connected to one of the aromatic ring's carbon atoms.
VIII.
IX. During the experiment, the students found that Alcohols that were used in the experiment are
mostly soluble in water. Alcohols may engage with water molecules more readily than
hydrocarbons of comparable molecular weight because alcohols and phenols may form
hydrogen bonds whereas hydrocarbons cannot. Alcohols and phenols are hence more water
soluble than hydrocarbons with equal molecular masses. 
X.
XI. The students made use of a lucas test. It is implied that a lucas test is when a chloroalkane is
produced, a clear and colorless property of the solution changes to a turbid, foggy, and hazy
one.  Based on how they react with the Lucas reagent, alcohols are divided into primary,
secondary, and tertiary categories. In contrast, To determine if an alcohol has a carbonyl
chemical group, students performed the iodoform test during the experiment. A very light
yellow precipitate of triiodomethane is produced when iodine and the base combine with
iodoform. 
XII.
XIII. Testing for the presence of aromatic compounds is done using the ferric chloride method. The
displacement of the chloride anions by the aromatic rings causes ferric chloride and aromatic
alcohol to react and produce a purple solution. Neither aliphatic alcohols nor ferric chloride
will interact, which explains why isopropyl and phenol results in a clear yellowish solution
when reacted witQUESTIONS

XIV. CONCLUSION
REFERENCES