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 questionQuestion
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
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
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.
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.
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.
Step-by-Step Method for Recrystallisation (Steps 7 & 8)
5 Marks • Assessment Objective: AO3 (Required Practical 10a)
✅ Full Mark Scheme Procedure
- M1: Dissolve the crude product in the minimum / small volume of hot methanol / solvent (or dissolve to form a saturated hot solution).
- M2: Hot filtration using standard fluted gravity filter paper and a pre-heated funnel (not Büchner filtration).
- M3: Cool the filtrate and leave it to crystallise (e.g. in an ice bath).
- M4: Filter under reduced pressure (using a Büchner funnel and suction flask).
- 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).
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.
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.
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 ).
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.