AQA A-Level Chemistry Paper 2, June 2025: Question 4

14 marks · Medium difficulty · Practical Techniques & Data Analysis

Describe the purification of hexanedioic acid by recrystallisation, evaluate errors in a melting point apparatus setup, and assess the sustainability of an alternative synthetic route from glucose.

Practise this question

Question

Multi-part practical exam question on the synthesis of hexanedioic acid from cyclohexanol and concentrated nitric acid. Part 1 asks why a fume cupboard is needed. Part 2 asks for the role of concentrated nitric acid. Part 3 asks to outline steps for recrystallisation and washing/drying to obtain purified crystals. Part 4 asks why ice-cold water is needed. Part 5 shows Figure 4, a student apparatus setup for measuring the melting point using a boiling tube containing water, a thermometer, and a sample tube held by a rubber ring, heated by an external flame, asking to identify two mistakes and their effects. Part 6 shows Figure 5, a two-stage reaction converting glucose to hexanedioic acid via E. coli bacteria followed by hydrogenation with H2/Pt, asking for sustainability justifications.
Question text

04 Hexanedioic acid is an important compound used in organic synthesis.

Hexanedioic acid can be prepared from cyclohexanol.

The equation for the reaction is

C6H11OH(l) + 2HNO3(aq) ⟶ HOOC(CH2)4COOH(s) + N2O(g) + 2H2O(l)

Method

Step 1 Add 5 cm3 of concentrated nitric acid to a boiling tube.

Step 2 Place the boiling tube in a beaker of water at 85 °C

Step 3 Add 2 cm3 of cyclohexanol dropwise to the boiling tube.

Step 4 Leave the reaction mixture for 10 minutes.

Step 5 Cool the boiling tube in a beaker of cold water for a further 10 minutes.

Step 6 Filter the contents of the boiling tube and collect the impure solid.

Step 7 Recrystallise the impure solid using methanol.

Step 8 Wash the purified crystalline product with some

ice-cold distilled water, and dry.

Step 9 Measure the melting point of the hexanedioic acid.

04.1 Suggest why the apparatus should be set up in a fume cupboard.

[1 mark]

04.2 Deduce the role of the concentrated nitric acid in the reaction.

[1 mark]

04.3 Outline how Steps 7 and 8 should be done to obtain the purified crystalline product.

[5 marks]

04.4 In Step 8, the distilled water must be ice-cold.

Suggest why using water at room temperature lowers the recorded yield of product.

[1 mark]

04.5 Figure 4 shows how a student set up the apparatus for measuring the melting point of

hexanedioc acid in Step 9 (data book value 152 °C).

The apparatus is supported by clamps but these are not shown.

Figure 4

Identify two mistakes the student made in setting up this apparatus.

State the problem caused by each mistake.

[4 marks]

Mistake 1

Problem caused

Mistake 2

Problem caused

Figure 5 shows an alternative process to make hexanedioic acid.

Figure 5

04.6 Scientists disagree about whether this alternative process is more sustainable or

less sustainable than the process starting from cyclohexanol.

Use the information given in Figure 5 to provide a justification for each point of view.

[2 marks]

Justification for alternative process being more sustainable

Justification for alternative process being less sustainable

Mark scheme

Show the mark scheme Mark scheme showing accepted answers: 04.1 requires identifying toxic/harmful/irritant/corrosive properties of gases or reagents such as N2O; 04.2 states oxidising agent; 04.3 awards 5 marks for dissolving in minimum volume of hot solvent, hot filtration, cooling to crystallise, filtration under reduced pressure, and drying; 04.4 explains that room-temperature water would dissolve the product; 04.5 identifies water boiling below the melting point of 152 °C and the sample placed too high relative to the thermometer bulb; 04.6 gives sustainability points for renewable glucose/E. coli vs multi-stage or high-pressure non-renewable hydrogen.

Question Answers Additional comments/Guidelines Mark

N2O is unknown so should be treated as a toxic Allow

N2O / cyclohexanol / methanol / nitric acid is

or N2O can cause respiratory problems 1

04.1 harmful / irritant / corrosive / toxic

(1 x AO3)

04.2 Oxidising agent

(1 x AO2)

– A-LEVEL CHEMISTRY – 7405/2 –

M1 Dissolve in minimum / small volume of hot methanol/solvent M1 allow Dissolve in hot methanol/solvent to

make saturated solution

M2 Hot Filtration (not Buchner)

M3 Cool/ leave (to crystallise) 5

04.3

(5 x AO3)

M4 Filter (under reduced pressure)

M5 Dry between filter papers or in a warm place

(Use of water at room temperature) dissolves product

04.4

OR Use of ice cold water prevents / reduces amount of product that (1 x AO2)

dissolves

– A-LEVEL CHEMISTRY – 7405/2 –

Mistake: no stirrer is in the boiling tube or

Mistake: Water is being used to warm sample

boiling tube used instead of D-tube / Thiele tube

Problem caused: Temperature will not reach high enough (to melt

sample) Problem caused: variation in temperature 4

04.5

(4 x AO3)

Mistake: Sample is much higher than bottom of thermometer

Problem caused: Temperature of sample will be lower / different 23

than reading on the thermometer

Reason process is more sustainable:

Any one from

• Glucose is a renewable resource / feedstock

• Biological reactant / E. coli bacteria is renewable

• Pt catalyst can be re-used

• Higher atom economy

04.6

(2 x AO3)

Reason process is less sustainable:

Any one from

• Synthesis is a 2-stage process

• Hydrogen gas is a non-renewable

• High pressures (are required in Stage 2)

• Uses a Pt catalyst that has been mined from the earth

How to answer it

Synthesis, Purification & Analysis of Hexanedioic Acid

📌 What This Question Tests

Core Required Practical Skills (RPA 10a & 10b) & Organic Chemistry Principles:

  • Laboratory Safety: Risk assessment and identifying hazards requiring a fume cupboard.
  • Redox Classifications: Recognising oxidising agents in organic preparations.
  • Purification by Recrystallisation: The precise 5-stage procedure (minimum hot solvent, hot filtration, cooling, Buchner filtration, drying).
  • Maximising Yield: Understanding solvent solubility and the rationale for ice-cold washing.
  • Melting Point Apparatus Evaluation: Identifying apparatus setup flaws (heating medium, tube placement) and their thermal consequences.
  • Green Chemistry & Sustainability: Evaluating industrial vs. bio-synthetic pathways using feedstock renewability, atom economy, and reaction conditions.
Question 04.1

Safety Rationale: Use of a Fume Cupboard

1 Mark • Assessment Objective: AO3

✅ Correct Answer

Any one of the following valid hazard statements:

  • N₂O is of unknown toxicity so should be treated as toxic / can cause respiratory problems.
  • Gases or vapours released (N₂O, cyclohexanol, methanol, or concentrated HNO₃) are toxic, corrosive, harmful, or respiratory irritants.

❌ Common Errors

  • Too vague: Stating simply that chemicals "are dangerous" or "smell bad" scores 0 marks.
  • Wrong hazard: Calling concentrated nitric acid merely "flammable" instead of corrosive/oxidising.
Mark Scheme: 1 mark for identifying that N₂O / cyclohexanol / methanol / nitric acid is toxic / harmful / corrosive / causes respiratory problems.
Question 04.2

Deducing the Role of Concentrated Nitric Acid

1 Mark • Assessment Objective: AO2

✅ Correct Answer

Oxidising agent (or oxidant).

💡 Key Knowledge

Cyclohexanol (a secondary alcohol, C₆H₁₁OH) is converted into a dicarboxylic acid, HOOC(CH₂)₄COOH.

  • This requires breaking a C–C bond and increasing the oxidation state of the carbon atoms from 0 to +3.
  • Concentrated HNO₃ is reduced (N goes from +5 in HNO₃ to +1 in N₂O), confirming it acts as an oxidising agent.

❌ Common Errors

  • Writing "catalyst" or "dehydrating agent" — concentrated HNO₃ is a stoichiometric reactant (consumed in a 2:1 ratio), not a catalyst.
  • Writing "acid" or "proton donor" — while it is an acid, its functional chemical role in this conversion is oxidation.
Mark Scheme: 1 mark for strictly "Oxidising agent".
Question 04.3

Step-by-Step Method for Recrystallisation (Steps 7 & 8)

5 Marks • Assessment Objective: AO3 (Required Practical 10a)

✅ Full Mark Scheme Procedure

  1. M1: Dissolve the crude product in the minimum / small volume of hot methanol / solvent (or dissolve to form a saturated hot solution).
  2. M2: Hot filtration using standard fluted gravity filter paper and a pre-heated funnel (not Büchner filtration).
  3. M3: Cool the filtrate and leave it to crystallise (e.g. in an ice bath).
  4. M4: Filter under reduced pressure (using a Büchner funnel and suction flask).
  5. M5: Dry the crystals between sheets of filter paper, in a desiccator, or in a warm oven / warm place.

🧠 Exam Technique & Keywords

  • Always specify "minimum" volume: Too much hot solvent prevents crystals from precipitating upon cooling, drastically lowering yield.
  • Distinguish the two filtration steps clearly:
    • Filtration 1 (Hot): Removes insoluble impurities. Must be gravity filtration so premature crystallisation does not block the funnel.
    • Filtration 2 (Cold): Collects the pure solid crystals, leaving soluble impurities in the cold filtrate. Done under reduced pressure for speed and dryness.

❌ Common Student Pitfalls

  • Omitting the word "minimum" or "hot" when describing dissolving (loses M1).
  • Confusing the filtration types (e.g. attempting Büchner filtration while hot, which causes rapid cooling and crystallization in the stem).
  • Forgetting to state drying at the end (loses M5).
Mark Breakdown: 1 mark per distinct operational stage (M1 to M5). Full 5 marks awarded for sequentially describing all five stages with precise terminology.
Question 04.4

Effect of Wash Water Temperature on Recorded Yield

1 Mark • Assessment Objective: AO2

✅ Correct Answer

  • Water at room temperature would dissolve some of the product / crystals (causing it to be lost in the filtrate).
  • OR: Ice-cold water minimises / prevents the dissolution of the product.

💡 Key Principle

Hexanedioic acid has two polar –COOH groups, meaning it has moderate solubility in water. Solubility increases with temperature. Washing with room-temperature water washes pure crystals away into the suction flask, reducing the final mass obtained.

Mark Scheme: 1 mark for stating that room temperature water dissolves product OR ice-cold water reduces/prevents dissolving.
Question 04.5

Critique of Melting Point Determination Apparatus

4 Marks (2 × 2 marks) • Assessment Objective: AO3

💡 Context: Data Book Melting Point = 152 °C

In Figure 4, the student placed a capillary melting point tube containing hexanedioic acid into a boiling tube filled with water over a heat source, with the sample positioned significantly above the thermometer bulb.

✅ Mistake 1 & Problem Caused

Mistake: Water is used as the heating liquid / bath.

Problem: Water boils at 100 °C, so it cannot reach the melting point of 152 °C (the sample will never melt).

Alternative: Mineral oil should be used instead of water.

✅ Mistake 2 & Problem Caused

Mistake: The sample is positioned significantly higher than the bulb of the thermometer (not level with it).

Problem: The thermometer will measure the temperature of a different region of liquid; the temperature recorded will be different / lower than the true temperature of the sample.

Alternative Mistake: No stirrer used / boiling tube used instead of Thiele tube → Problem: Uneven heat distribution / temperature variation.

❌ Examiner Trap: Rubber Ring Positioning

Students often incorrectly claim the rubber ring is submerged or burning. In this diagram, the rubber ring is well above the water level. Stick to the two catastrophic errors: wrong liquid (water boils at 100 °C vs 152 °C mp) and sample not level with the thermometer bulb.

Mark Breakdown: 1 mark for each identified mistake + 1 mark for its matching consequence (Total 4 marks).
Question 04.6

Evaluating Pathway Sustainability

2 Marks • Assessment Objective: AO3

✅ Justification: MORE Sustainable (Any 1)

  • Glucose is a renewable resource / renewable feedstock (whereas cyclohexanol is derived from crude oil).
  • Biological catalyst / E. coli bacteria is a renewable resource operating under mild biological conditions.
  • Platinum (Pt) catalyst can be reused / recycled.
  • Higher atom economy in Stage 2 (addition of H₂ has 100% atom economy).

✅ Justification: LESS Sustainable (Any 1)

  • Synthesis requires a two-stage process (the original is single-stage).
  • Hydrogen gas (H₂) is non-renewable (currently sourced from fossil fuels / steam reforming of methane).
  • High pressure is required in Stage 2 (350 kPa), which consumes significant energy and requires specialised pressure vessels.
  • Uses a Platinum (Pt) catalyst, a scarce transition metal that must be extracted/mined from the Earth.

🧠 How to Tackle Sustainability Comparisons

Always inspect the reaction conditions and reagents shown in the scheme:

  • Look at starting materials: Glucose = plants/crops = renewable. Cyclohexanol = petrochemicals = non-renewable.
  • Look at reaction conditions: Stage 2 uses 350 kPa and 360 K . High pressures require compressors that consume electrical energy.
  • Look at reagents: H₂ is typically derived from fossil fuels ( CH₄ + H₂O → CO + 3H₂ ).
Mark Scheme: 1 mark for a valid "more sustainable" reason + 1 mark for a valid "less sustainable" reason based on Figure 5.

Topics

Organic Chemistry · Required Practicals · 3.3.5 Alcohols · 3.3.14 Organic Synthesis · Required Practical 10: Preparation of a pure organic liquid · Required Practical 12: Separation and purification techniques

Question and mark scheme from the AQA A-Level Chemistry examination, Paper 2, June 2025. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.