Chromatography and tests for functional groups Module 6

Where it is examined
A-level Paper 2 and Paper 3
Level
A level only
Specification
Section 6.3.1, 12 learning outcomes
Since 2016
31 question parts: 6 multiple choice, 4 calculations, 3 six-mark level of response

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Learning outcomes

Show the 12 learning outcomes from the specification

Six-mark level of response questions on this topic

SeriesPaperQWhat it asks
June 2024Paper 35(b)(ii)The student is provided with further information about compounds F–I. Use this further information and the student’s observations in Table 5.1 to answer the following.
November 2021Paper 221Compounds D, E and F are isomers with the molecular formula C5H10O. Analyse the observations and results to identify the structures of D, E and F.
June 2017Paper 35(b)The structures for six naturally occurring organic compounds with pleasant smells, B–G, are Explain how chemical tests would allow each compound to be distinguished from the other

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June 2025 · Paper 2 · Q21(b) 2 marks Short answer Easy
Earlier part of question 21 that this part usesEarlier part of June 2025 Paper 2 question 21
(b) A chemical test is carried out which gives a positive result for all three compounds.
Suggest the reagent and observation of this chemical test.
Reagent ............................................................................................................................................
Observation  ......................................................................................................................................
[2]
June 2025 · Paper 2 · Q21(c) 3 marks Complete table/diagram Hard
Earlier part of question 21 that this part usesEarlier part of June 2025 Paper 2 question 21
(c) A student is provided with three unlabelled sample tubes, containing either pyruvic acid,
methylglyoxal or acetol.
The student carries out three chemical tests on each sample.
Complete the table with the expected observations, including ‘no change’ where appropriate.
Expected observations
Chemical test
Pyruvic acid Methylglyoxal Acetol
Tollens’ reagent
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Na2CO3(aq)
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Cr2O7 2–(aq)/H+(aq)
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[3]
June 2025 · Paper 2 · Q22(a)(i) 1 mark Short answer Medium
22 This question is about organic acids.
α-Amino acids have the general formula RCH(NH2)COOH.
(a) Compound S is made of two α-amino acids bonded together.
Compound S is hydrolysed into its component α-amino acids.
The resulting mixture is analysed using TLC to produce a chromatogram:
solvent front
start line
The R group and the Rf value is shown for some α-amino acids.
R group Rf value
–H 0.18
–CH3 0.25
–CH2CH(CH3)2 0.64
–CH(CH3)2 0.77
(i) Determine the Rf values of the two α-amino acids in the chromatogram.
[1]
June 2025 · Paper 2 · Q22(a)(ii) 2 marks Drawing / labelling Medium
Earlier part of question 22 that this part usesEarlier part of June 2025 Paper 2 question 22
(ii) Compound S has two possible structures.
Draw both of these structures.
[2]
June 2025 · Paper 3 · Q2(b)(i) 1 mark Short answer Easy
(b) Nuromol tablets are used to relieve pain.
Nuromol tablets contain a mixture of ibuprofen and paracetamol.
The structures of ibuprofen and paracetamol are shown.
H3C OH
CH2
O O
CH
C C
CH3
OH H3C N
CH
H
CH3
Ibuprofen Paracetamol
A student carries out an investigation to determine the mass of ibuprofen and the mass of
paracetomol in one nuromol tablet.
• Ibuprofen reacts with aqueous sodium carbonate, Na2CO3(aq), to produce a gas.
2RCOOH  +  Na2CO3 2RCOONa  +  CO2  +  H2O
• Paracetamol does not react with Na2CO3(aq).
(i) Why does paracetamol not react with Na2CO3(aq)?
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June 2024 · Paper 2 · Q3 1 mark Multiple choice Medium
3 A student investigates the rate of hydrolysis of different iodoalkanes using aqueous silver nitrate
in ethanol.
What colour of precipitate is seen?
A Brown
B Cream
C White
D Yellow
Your answer
[1]
June 2024 · Paper 2 · Q5 1 mark Multiple choice Medium
5 Geraniol, shown below, is a component in many natural oils.
OH
Geraniol
Which pair of reagents identifies both functional groups in geraniol?
A Acidified dichromate(VI) and 2,4-dinitrophenylhydrazine.
B Bromine water and 2,4-dinitrophenylhydrazine.
C Bromine water and acidified dichromate(VI).
D Tollens’ reagent and aqueous silver nitrate in ethanol.
Your answer
[1]
June 2024 · Paper 2 · Q13 1 mark Multiple choice Medium
13 A sample containing a mixture of 3 components, X, Y and Z, is analysed using gas
chromatography.
The gas chromatogram below is obtained.
The relative peak areas of X, Y and Z are included.
Z
Relative peak areas
X = 1.0
1000 Y
Y = 3.5
Z = 5.5
X
Recorder response
500
0
0 5 10 15
Time / min
Which statement(s) is/are true?
1 The peak for component X shows the mass of one mole.
2 Component Y stays in the column for longer than component X.
3 Component Z consists of more than half of the sample.
A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer
[1]
June 2024 · Paper 3 · Q5(a)(i) 1 mark Calculation Easy
5 This question is about the analysis of organic compounds.
(a) A student investigates the alkaline hydrolysis of 1-bromopropane as outlined below.
Step 1 The student adds 1-bromopropane to an excess of aqueous potassium hydroxide,
KOH(aq), in a pear-shaped flask.
Step 2 A TLC chromatogram is run using propan-1-ol and the reaction mixture.
Step 3 The reaction mixture is refluxed.
A TLC chromatogram of the reaction mixture is run every 10 minutes.
The TLC chromatograms are shown below.
Before reflux After 10 minutes After 20 minutes After 30 minutes
solvent
front
origin
propan-1-ol reaction mixture propan-1-ol reaction mixture propan-1-ol reaction mixture propan-1-ol reaction mixture
(i) Determine the Rf value of propan-1-ol.
Show your working.
Rf = ................... [1]
June 2024 · Paper 3 · Q5(a)(iii) 3 marks Short answer Easy
Earlier part of question 5 that this part usesEarlier part of June 2024 Paper 3 question 5
(iii) A student investigates the alkaline hydrolysis of 1-chloropropane using the same method as for
1-bromopropane.
Predict, with reasons, how the appearance of the reaction mixture in the chromatogram produced
after 20 minutes would be different when 1-chloropropane is used instead of 1-bromopropane.
Suggest why propan-1-ol is run alongside the reaction mixture.
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June 2024 · Paper 3 · Q5(b)(ii) 6 marks 6-mark level of response Easy
Earlier part of question 5 that this part usesEarlier part of June 2024 Paper 3 question 5
(ii)* The student is provided with further information about compounds F–I.
• They all have the molecular formula C5H10O.
• One of the compounds is alicyclic.
• The other compounds are unbranched.
Use this further information and the student’s observations in Table 5.1 to answer the following.
• How do the observations provide evidence for the possible functional groups in
compounds F–I?
• Suggest a possible structure for each of the compounds F–I.
Show your reasoning. [6]
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June 2023 · Paper 2 · Q2 1 mark AO1 Multiple choice Medium
2 Which compound reacts with 2,4-dinitrophenylhydrazine but does not react with Tollens’
reagent?
A C6H5COCOOH
B C6H5CH(OH)CHO
C CH3COCHO
D CH3CH2CH(OH)CH3
Your answer
[1]
June 2022 · Paper 2 · Q18(a)(i) 3 marks AO1 Short answer Medium
18 This question is about carbonyl compounds.
(a) (i) Describe a chemical test to confirm the presence of a carbonyl group.
How could the product of this test be used to identify the carbonyl compound?
Your answer should not include spectroscopy.
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June 2022 · Paper 2 · Q18(a)(ii) 1 mark AO1 Short answer Easy
Earlier part of question 18 that this part usesEarlier part of June 2022 Paper 2 question 18
(ii) Describe a chemical test that would identify whether a carbonyl compound is an
aldehyde.
Your answer should include the reagent and observations.
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June 2022 · Paper 2 · Q20(a)(i) 1 mark AO1 Short answer Hard
20 This question is about the chemistry of aromatic compounds.
(a) Compounds J, K and L, shown below, are structural isomers.
CH3
CH2CH2OH OH H3C OH
CH3 CH3
Compound J Compound K Compound L
(i) What chemical test(s) could be used to confirm the presence of the phenol group in
compounds K and L?
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November 2021 · Paper 2 · Q10 1 mark Multiple choice
10 A TLC chromatogram for two compounds is shown below.
solvent front
origin
What is the Rf value for the compound that is most strongly adsorbed onto the stationary phase?
A 0.25
B 0.33
C 0.69
D 0.78
Your answer
[1]
November 2021 · Paper 2 · Q21 6 marks AO3 6-mark level of response
21* Compounds D, E and F are isomers with the molecular formula C5H10O.
One of the compounds is alicyclic.
A student carries out test-tube tests on the compounds.
The observations are shown below.
Compound 2,4-DNP H+/Cr2O7 2–, reflux Bromine water
D No change Green solution No colour change
Orange
E No colour change No colour change
precipitate
Orange
F No colour change No colour change
precipitate
13C NMR spectrum of D Compound D has 3 peaks at δ / ppm: 24, 36, 73.
1H NMR spectra of E and F The integration data has been omitted.
Compound E
3 2 1 0
chemical shift, δ / ppm
Compound F
Expansion of multiplet
3 2 1 0
chemical shift, δ / ppm
Analyse the observations and results to identify the structures of D, E and F.
Explain your reasoning. [6]
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November 2020 · Paper 2 · Q13 1 mark AO1 Multiple choice
13 Which statement(s) is/are correct for gas chromatography?
1 The components in a mixture can be identified from their retention time.
2 The relative peak areas give the proportions of components in a mixture.
3 Calibration curves are used to confirm the concentrations of components in a mixture.
A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer
[1]
November 2020 · Paper 2 · Q19(b) 4 marks AO2, 3 Short answer Hard
Earlier part of question 19 that this part usesEarlier part of November 2020 Paper 2 question 19
(b) Describe suitable chemical tests, with observations, that would confirm the presence of the
functional groups in F and G.
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June 2019 · Paper 2 · Q16(b)(i) 2 marks AO1 Short answer Easy
(b) Geraniol and citronellal, shown below, are isomers present in ‘citronella oil’, used as an insect
repellent.
OH
O
Geraniol Citronellal
• Geraniol and citronellal are structural isomers of each other.
• They also show stereoisomerism.
(i) Describe how the observations from a chemical test would distinguish between geraniol
and citronellal.
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June 2019 · Paper 2 · Q17(b)(i) 1 mark AO1 Calculation Easy
Earlier part of question 17 that this part usesEarlier part of June 2019 Paper 2 question 17
(b) The student is provided with another amino acid.
The student attempts to identify the unknown amino acid using chromatography.
The student obtains two TLC chromatograms of the unknown amino acid and the four amino
acids in Table 17.1, using two different solvents, W and X.
solvent  front
origin
unknown ala ser leu gly unknown ala ser leu gly
amino amino
acid acid
Solvent W Solvent X
(i) What is the Rf value of serine (ser) in solvent W?
Rf =  ......................................................... [1]
June 2019 · Paper 2 · Q17(b)(ii) 2 marks AO2 Data interpretation Easy
Earlier parts of question 17 that this part usesEarlier part of June 2019 Paper 2 question 17Earlier part of June 2019 Paper 2 question 17
(ii) Analyse the chromatograms to identify the unknown amino acid.
Explain your reasoning.
Name of unknown amino acid  ...........................................................................................
Explanation  .......................................................................................................................
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June 2019 · Paper 2 · Q18(c) 1 mark AO3 Structure / isomer Medium
Earlier part of question 18 that this part usesEarlier part of June 2019 Paper 2 question 18
(c) Compound B is a structural isomer of ester A.
• Compound B reacts with aqueous sodium carbonate.
• The 13C NMR spectrum of B has 4 peaks.
Draw a possible structure for compound B.
[1]
June 2019 · Paper 3 · Q4(a)(iii) 2 marks AO1, 2 Short answer Hard
Earlier part of question 4 that this part usesEarlier part of June 2019 Paper 3 question 4
(iii) Name the functional group responsible for the acidity of chloroxylenol and describe a
simple test which would confirm the presence of this group.
Functional group ................................................................................................................
Test  ....................................................................................................................................
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June 2018 · Paper 2 · Q19(c)(ii) 3 marks Calculation Hard
Earlier part of question 19 that this part usesEarlier part of June 2018 Paper 2 question 19
(ii) Analyse the information to identify E, F and G.
Show your working.
[3]
June 2018 · Paper 2 · Q20(b)(i) 1 mark Short answer Easy
Earlier part of question 20 that this part usesEarlier part of June 2018 Paper 2 question 20
(b) A student plans to carry out some chemical tests on both cinnamaldehyde and
methylcinnamaldehyde.
CHO CHO
cinnamaldehyde methylcinnamaldehyde
(i) Suggest a suitable chemical test to confirm that both compounds contain an unsaturated
carbon chain.
Your answer should include the reagent and observations.
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June 2018 · Paper 2 · Q20(b)(ii) 1 mark Short answer Easy
Earlier part of question 20 that this part usesEarlier part of June 2018 Paper 2 question 20
(ii) Describe a chemical test to confirm that both compounds contain an aldehyde functional
group.
Your answer should include the reagent and observations.
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June 2018 · Paper 2 · Q20(b)(iii) 3 marks Short answer Medium
Earlier part of question 20 that this part usesEarlier part of June 2018 Paper 2 question 20
(iii) Describe a chemical test to confirm that cinnamaldehyde and methylcinnamaldehyde
contain a carbonyl group.
How could the products of this test be used to distinguish between the two compounds?
Your answer should not include spectroscopy.
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June 2018 · Paper 2 · Q21(c)(i) 2 marks Calculation Medium
(c) A cosmetic product containing four esters, J, K, L and M, is analysed by gas chromatography
and mass spectrometry. The results are shown below.
Gas chromatogram
M
5.9
K
J
4.3
4.2
L
1.0
0 1 2 3 4 5
retention time / minutes
The numbers by the peaks are the relative molar proportions of the compounds in the mixture.
Mass spectrometry
ester m/z of molecular ion peak
J 152
K 166
L 180
M 180
(i) The concentration of ester K in the cosmetic product is 9.13 × 10−2 g dm−3.
Using the results, calculate the concentration, in mol dm−3, of ester M in the cosmetic
product.
Give your answer to two significant figures.
concentration of ester M =  .......................................... mol dm−3 [2]
June 2017 · Paper 2 · Q20(b) 3 marks Short answer
Earlier part of question 20 that this part usesEarlier part of June 2017 Paper 2 question 20
(b) Qualitative tests are carried out on the aromatic compound. The results are shown below.
Test Acidity Na2CO3(aq) 2,4-DNP Tollens’ reagent
No observable No observable
Observation pH = 5 Orange precipitate
change change
Determine the functional groups in the compound. Explain your reasoning.
Functional groups  .....................................................................................................................
Explanation  ...............................................................................................................................
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June 2017 · Paper 3 · Q5(b) 6 marks 6-mark level of response
(b)* The structures for six naturally occurring organic compounds with pleasant smells, B–G, are
shown below. The common names in brackets relate to their source and smell.
OH
O
B C
(linalool) (citral)
O
OH
D
(geraniol)
E
(camphor)
O
OH
F G
(menthol) (ionone)
Explain how chemical tests would allow each compound to be distinguished from the other
compounds.
In your answer, include essential details for all test procedures and observations.
Details of apparatus and quantities are not required.
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