CIE Chemistry A-Level

Practicals for Papers 3 and 5

Organic Analysis Practicals

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Chromate VI and Dichromate VI

Note​​:
​​ 2-​​
● Chromate VI is ​CrO​​4​2-​ ​ . Dichromate VI is ​Cr​​2​O​
​ ​7​​ .
● K​2​CrO​4 is
​ ​yellow​​. K​2​Cr​2​O​7 is
​ ​orange​​.

Test for an alcohol: using potassium dichromate (or chromate)

1. To distinguish between different types of alcohols, add ​acidified​​ potassium dichromate to the
solution.
2. Primary and secondary alcohols will reduced from orange dichromate (VI) ions to ​green
chromium (III) ions. (Chromate (VI) also goes green.)
3. It will remain orange if a ​tertiary​​ alcohol is present.

Reaction tips

● If no colour change occurs, try ​gently​​ heating the mixture. However, don’t heat excessively
as it may evaporate the alcohol or other organic liquid. Heating should cause a rapid colour
change.
● Also, use a ​small​​ mass of chromate/dichromate because if used in excess, the colour will
remain yellow/orange from the remaining unoxidised chromate/dichromate will mask any
green colour from the alcohol present. A small amount ensures ​all ​of the
chromate/dichromate will react if the alcohol is present.

Test for an alcohol: using metal

1. Add a small piece of metallic ​sodium​​ to alcohol.

2. Produces ​hydrogen​​ gas which is shown by ‘squeaky pop’ test.
3. Dispose any excess sodium ​safely​​ using the beaker of ethanol provided. (Sodium will
completely react with the excess ethanol in order to be safely washed away because if any water
comes into contact with the sodium there is a ​serious fire risk​​).

Test for an aldehyde: Fehling’s solution

1. In a clean test tube mix together equal volumes of ​Fehling's solution​​ A (blue aqueous solution
of copper (II) sulfate pentahydrate crystals) and Fehling's solution B (clear solution of aqueous
potassium sodium tartrate and a strong alkali). The resultant Fehling's test reagent should be a
clear ​dark blue​​ ​solution​​.
2. Add 5 drops of this test reagent to a test tube along with a few ​anti-bumping granules​​, and
then add the aldehyde.
3. ​Warm gently​​ for around two minutes in a beaker of hot water, gradually bring the beaker of
water to boiling and maintain this temperature for a few minutes.
4. Carefully lift the test tube out of the boiling water and allow its contents to stand for several
minutes.

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5. A​ brick red precipitate​​ formed if an aldehyde is present.

Test for an alkene: bromine water

1. Add about 1 cm3 of bromine water to 2 drops alkene.

2. Shake the contents of the tube vigorously from side to side.
3. Bromine water ​decolourised from orange​​ if an alkene is present.

Test for a carboxylic acid: sodium carbonate

1. Place spatula of solid ​sodium carbonate​​ in a test tube and add about 2 cm​3​ of dilute ethanoic
acid using a pipette.
2. Collect the gas produced and bubble through limewater (calcium hydroxide). It will turn cloudy if
a carboxylic acid is present as ​CO​​2​​ is produced. (Phenols are also acidic but are not sufficiently
acidic to react with carbonates.)

Test for a halogenoalkane: sodium hydroxide and silver nitrate

1. Using a teat pipette, add 5 drops of 1-bromobutane to about 1cm3 of ​sodium hydroxide
solution in a test tube. (OH- ions replace the Br by ​nucleophilic substitution​​).
2. ​Warm​​ the contents of the test tube for a few minutes in a beaker filled with hot water at
approximately 60°C.
3. Acidify the contents of the test tube by adding 2cm3 of ​dilute nitric acid ​and then add about
1cm3 of silver nitrate solution. (Nitric acid removes carbonate and hydroxide impurities which
would form ​precipitates​​. Silver Bromide precipitate then forms).

Thin layer chromatography

Method Accuracy Explanation
1) Wearing gloves carefully use a ● Gloves ● Gloves​​ prevent
pencil to draw a faint line ​1 cm ● Pencil line contamination from the hands
above​​ the bottom of a TLC plate to the plate
and mark five spots, equally ● Pencil ​line –will not dissolve
spaced, along this line. in the solvent

2) Use a capillary tube to apply a Tiny ​drop Too big a drop will cause different
tiny drop of each solution to a spots to merge
different origin spot and allow the
plate to ​air dry​​. If required repeat
this process to achieve small but
concentrated spots

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3) Add approximately 10 cm​3​ of Depth of solvent If the solvent is too deep it will
solvent to a development dissolve​​ the sample spots from the
chamber (or suitable container plate.
with a lid)
4) Place the TLC plate into the Lid To prevent evaporation of toxic
development chamber​​, making solvent and so that the inside of the
sure that the level of the solvent tank is saturated with the solvent
is below the spotting line. vapour.
Replace the lid and make sure it
is a tight seal.
5) When the level of the solvent ● Allow solvent ● Will get more accurate results
reaches about 1 cm from the top line to rise if the solvent is allowed to rise
of the plate, remove the plate near​​ to the top to near the top of the plate
and mark the ​solvent front​​ with of the plate but the Rf value can be
a pencil. Allow the plate to dry in ● Dry in fume calculated if the solvent front
the fume cupboard. cupboard does not reach the top of the
plate
● Dry in a fume cupboard as
the solvent is toxic

6) Place the plate under a UV UV lamp UV lamp used if the spots are
lamp in order to visualise the colourless and not visible.
spots. Draw around them ​lightly
in pencil.

7) Calculate the Rf​ values

​ of the Use mm ruler Higher resolution - more precise ​Rf
observed spots. value​​ calculated

N.B
● If you use less solvent and have a high baseline you will get large spots
● If your sample is too concentrated then your spots overlap

Melting Points

Melting point of synthesised product:

● If the sample is very pure then the melting point will be ​sharp​​ (same value as quoted in
data books).
● If impurities are present (and this can include solvent from the recrystallization process) the
melting point will be​ lowered​​ and the sample will ​melt over a range​​ of several degrees.
● Can be measured in an electronic melting point machine or by using a practical set up
where the capillary tube is strapped to a thermometer immersed in some heating oil. In both
cases a small amount of the salt is put into a capillary tube. The tube is heated up and is
heated slowly when near the melting point​​.
● Compare​​ experimentally determined melting point value with one quoted in a data source
to determine purity.
● Error may occur if the temperature on the thermometer is not the same as the temperature
in the actual sample tube.

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Measuring boiling point of synthesised liquid:

● This can be done in a distillation set up or by simply boiling a tube of the sample in a
heating oil bath.
● Pressure​​ should be noted- changing pressure can change the boiling point of a liquid.
● Not the most accurate method of identifying a substance as several substances may have
the same boiling point.
● To get a correct measure of boiling point the thermometer should be ​above​​ the level of the
surface of the boiling liquid and be ​measuring the temperature of the saturated vapour​​.

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