AQA A-Level Chemistry Paper 2, 2017: Question 7

6 marks · Medium difficulty · Long Answer

Describe how to distinguish between four organic compounds containing carboxylic acid, alcohol, aldehyde, and halogenoalkane groups using the minimum number of test-tube reactions.

Practise this question

Question

Question 07.1 displays the chemical structures of four organic compounds labeled K, L, M, and N. Compound K is 2-hydroxypropanoic acid [CH3-CH(OH)-COOH], Compound L is 2-bromo-2-methylpropan-1-ol [(CH3)2C(Br)-CH2OH], Compound M is 2-methylpropanoic acid [(CH3)2CH-COOH], and Compound N is 2-bromo-2-methylpropanal [(CH3)2C(Br)-CHO]. The question asks to describe how to distinguish between all four compounds using the minimum number of tests on each compound, describing the observations in each test, for 6 marks.
Question text

07 Test-tube reactions can be used to identify the functional groups in organic

molecules.

07.1 You are provided with samples of each of the four compounds.

Describe how you could distinguish between all four compounds using the

minimum number of tests on each compound.

You should describe what would be observed in each test.

[6 marks]

Mark scheme

Show the mark scheme Mark scheme for question 07.1 giving a levels of response grid from Level 1 (1–2 marks) to Level 3 (5–6 marks). Stage 1 involves an initial test separating compounds into groups, Stage 2 separates further, and Stage 3 completely distinguishes all four. It lists appropriate reagents and observations: NaHCO3/Na2CO3 for -COOH (effervescence), acidified K2Cr2O7 for -OH and -CHO (turns orange to green), Fehling's or Tollens' reagent for -CHO (red precipitate or silver mirror), and silver nitrate for -Br (cream precipitate). A summary table maps which compounds react positively to each test.

07.1 This question is marked using Levels of Response. Refer to the Indicative Chemistry content

Mark Scheme Instructions for Examiners for guidance.

Stage 1: An initial test to separate into two groups (2 groups

Level 3 All stages are covered and each stage is generally of 2 OR 1 group of 3 and 1 group of 1)

correct and virtually complete.

5-6 marks Stage 2: An second test to distinguish within a group or to

Answer is communicated coherently and shows a separate into two further groups

logical progression from Stage 1 to Stages 2 and 3 to

distinguish all the compounds with results for all Stage 3: A third test leads to a set of results/observations

remaining compounds stated. which distinguishes between all 4 compounds

Describing subsequent organic test on product Tests must include reagent and observation which identifies

(unnecessary) - limits to lower mark in level compound(s)

-COOH

Level 2 All stages are covered but stage(s) may be incomplete

a) NaHCO3 / Na2CO3 (or correct alternative)

or may contain inaccuracies

3-4 marks b) effervescence /gas turns limewater milky

OR two stages are covered and are generally correct

c) K and /or M but not L and/or N

and virtually complete.

-OH and -CHO

Answer is communicated mainly coherently and shows d) acidified K2Cr2O7

a logical progression from Stage 1 to Stages 2 and 3. e) solution turns green

f) K and/or L and/or N but not M

Describing subsequent organic test on product

-CHO

(unnecessary) - limits to lower mark in level

g) Fehlings OR Tollens

h) red ppt OR silver mirror

Level 1 Two stages are covered but stage(s) may be incomplete

i) N only but not K and/or L and/or M

or may contain inaccuracies OR only one stage is

1-2 marks -Br

covered but is generally correct and virtually complete.

j) Silver nitrate

Answer includes isolated statements but these are not k) cream ppt

presented in a logical order. l) L and/or N but not K and/or M

Isolated tests on individual compounds– - max LEVEL 2––

0 mark Insufficient correct chemistry to gain a mark. Isolated tests not linked to any compound – max LEVEL 1

Penalise observation if deduction wrong, but allow

observation if deduction incomplete

23 of 32

Alternative tests

-COOH -COOH -OH only

a) named alcohol & H2SO4 a) named indicator m) named carboxylic acid & H2SO4

b) sweet smell (of ester) b) correct colour n) sweet smell (of ester)

c) K and /or M but not L and/or N c) K and /or M but not L and/or N o) K and/or L but not M and /or N

H CH3 CH3 CH3

H3C C COOH H3C C CH2OH H3C C COOH H3C C CHO

OH Br H Br

Test Tests

K L M N

for

a) NaHCO3 / Mg / Indicator K M × ×

d) K Cr O / H+ K L N ×

22 7

g) Fehlings / Tollens N × × ×

j) AgNO3 see Note * L N × ×

a) named alcohol & H2SO4 K M × ×

m) named carboxylic acid & K L × ×

H2SO4

Note * allow NaOH then HNO3, AgNO3 as one test; but treat NaOH, AgNO3 without acid as incomplete,so can mark on.

How to answer it

Distinguishing Organic Functional Groups (Extended Response)

WHAT THIS QUESTION TESTS

This 6-mark level-of-response question assesses your ability to devise a logical, sequential analytical pathway to distinguish four organic molecules using the minimum number of test-tube reactions.

  • Functional group identification: Recognizing carboxylic acids (-COOH), primary/secondary alcohols (-OH), aldehydes (-CHO), and haloalkanes (-C-Br).
  • Qualitative reagents & observations: Correctly specifying reagents (e.g., NaHCO₃, acidified K₂Cr₂O₇, Tollens' reagent) and recording positive and negative visible changes.
  • Practical logic (Levels of Response): Designing a branching scheme (e.g., separating into groups of 2, then differentiating within each group) rather than performing random, isolated tests.
QUESTION 07.1

Functional Group Audit of the Four Compounds

Identify what functional groups are present before choosing reagents

Compound Structure Functional Groups Present Reactivity Profile
K CH₃-CH(OH)-COOH Carboxylic acid & Secondary (2°) alcohol Acidic (reacts with carbonates); oxidisable by K₂Cr₂O₇
L (CH₃)₂C(Br)-CH₂OH Primary (1°) alcohol & Tertiary (3°) haloalkane Neutral; oxidisable by K₂Cr₂O₇; releases Br⁻ upon hydrolysis
M (CH₃)₂CH-COOH Carboxylic acid only Acidic (reacts with carbonates); resistant to oxidation
N (CH₃)₂C(Br)-CHO Aldehyde & Tertiary (3°) haloalkane Oxidisable by Tollens'/Fehling's & K₂Cr₂O₇; releases Br⁻ upon hydrolysis

Full-Mark Model Strategy (3-Stage Workflow)

A minimal, 3-test sequential branching scheme that reaches Level 3 (5–6 marks)

✅ Model Answer: Sequential Elimination Pathway

Stage 1: Add Sodium Hydrogencarbonate (NaHCO₃) or Sodium Carbonate (Na₂CO₃) solution
  • Observation: Effervescence / gas given off that turns limewater milky.
  • Result: Separates the carboxylic acids (K and M) from the non-acids (L and N).
  • Deduction: K and M give effervescence; L and N produce no reaction / no effervescence.
Stage 2: Distinguish between K and M using Acidified Potassium Dichromate(VI) (K₂Cr₂O₇ / H₂SO₄) and heat
  • Observation: Orange solution turns green.
  • Result for K: Turns green (contains a 2° alcohol which is oxidised to a ketone).
  • Result for M: Remains orange (no oxidisable group). Compound M is fully identified.
Stage 3: Distinguish between L and N using Tollens' Reagent (warm) or Fehling's Solution (warm)
  • Observation: Formation of a silver mirror (Tollens') OR red precipitate (Fehling's).
  • Result for N: Silver mirror formed / red ppt (aldehyde is oxidised). Compound N is fully identified.
  • Result for L: Solution remains colourless / stays blue (primary alcohol does not react with Tollens' or Fehling's). Compound L is fully identified.

All 4 compounds are uniquely identified in 3 tests.

Mark Scheme Level Breakdown:
• Level 3 (5–6 marks): All three stages covered; clear logical flow separating into groups and determining all compounds with fully stated positive and negative observations.
• Level 2 (3–4 marks): Two stages fully complete, or all stages covered but missing negative observations / containing errors.
• Level 1 (1–2 marks): Isolated tests with no linked logic.

💡 Key Knowledge: Test-Tube Reactions

  • Carboxylic acid (-COOH):
    Reagent: NaHCO₃(aq) or Na₂CO₃(aq).
    Observation: Effervescence / bubbles (CO₂ gas).
  • Aldehyde only (-CHO):
    Reagent: Tollens' reagent [Ag(NH₃)₂]⁺ (warm).
    Observation: Silver mirror.
    Or: Fehling's solution (warm) → brick-red precipitate.
  • Oxidisable group (1°/2° alcohol, aldehyde):
    Reagent: K₂Cr₂O₇ / H₂SO₄ (acidified potassium dichromate) and heat.
    Observation: Orange to green (Cr⁶⁺ reduced to Cr³⁺).
  • Bromoalkane (-Br):
    Reagent: Warm with NaOH(aq), acidify with dilute HNO₃, add AgNO₃(aq).
    Observation: Cream precipitate (AgBr).

🧠 Exam Technique & Examiner Insight

  • Never test blindly: The mark scheme specifically states: "Isolated tests on individual compounds – max LEVEL 2". You must test all remaining samples comparatively in each stage.
  • State both positive AND negative outcomes: To distinguish A from B, you must state what happens to A and what happens to B (e.g., "K turns green, M stays orange").
  • Don't test reaction products: The mark scheme warns: "Describing subsequent organic test on product (unnecessary) limits to lower mark in level". Only test the original samples provided!
  • Minimum tests rule: Using 4 different tests when 3 suffice wastes precious time and can limit your score.

❌ Common Pitfalls to Avoid

  • Trying to separate L and N using K₂Cr₂O₇ / H⁺: Both L (a 1° alcohol) and N (an aldehyde) turn acidified potassium dichromate from orange to green! This test does not distinguish between them. You must use Tollens' reagent or Fehling's solution.
  • Incomplete Haloalkane Reagent: If using silver nitrate to detect bromine, students often write just "add AgNO₃". You must first hydrolyse the haloalkane by warming with aqueous NaOH, then acidify with dilute HNO₃, before adding AgNO₃. Writing only "AgNO₃" or omitting "HNO₃" loses marks.
  • Vague observations: Writing "turns clear", "goes discoloured", or "colour change" receives zero credit. Always write precise colors: "orange to green" or "forms a silver mirror".
  • Confusing the alcohols in K and L: Compound K is a secondary alcohol (oxidised to a ketone; does not react with Tollens'). Compound L is a primary alcohol (does not react with Tollens' under mild conditions).

Topics

Organic Chemistry · Required Practicals · 3.3.6 Organic Analysis · 3.3.5 Alcohols · 3.3.8 Aldehydes and Ketones · 3.3.9 Carboxylic Acids and Derivatives · Required Practical 6: Tests for alcohol, aldehyde, alkene and carboxylic acid

Question and mark scheme from the AQA A-Level Chemistry examination, Paper 2, 2017. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.