AQA A-Level Chemistry AS Paper 2, June 2025: Question 6

16 marks · Medium difficulty · Practical Techniques & Data Analysis

Complete the reaction mechanism, calculations, practical distillation analysis, and combustion equations for the preparation and reactions of cyclohexanol.

Practise this question

Question

Question 06 consists of ten sub-questions: 06.1 asks to complete the balanced equation for the acid-catalysed hydration of cyclohexene to cyclohexanol; 06.2 asks to add curly arrows to an electrophilic addition mechanism involving cyclohexene, H+, and H2O; 06.3 asks to calculate the amount in moles of phosphoric acid in 6.0 cm³ of concentrated phosphoric acid (density 1.69 g/cm³, 85% H3PO4 by mass); Figure 2 shows an organic distillation apparatus with a sealed collection flask; questions 06.4 to 06.7 ask practical questions about water entering at the bottom of the condenser, the role of anti-bumping granules, why an electric heater is used, and why the closed distillation apparatus is dangerous along with a remedy; 06.8 asks for the mechanism name for the dehydration of cyclohexanol; 06.9 asks for a balanced equation for the complete combustion of cyclohexanol; 06.10 asks for the definition of carbon-neutral and why mixing cyclohexanol biofuel with diesel is not carbon-neutral.
Question text

06 Cyclohexanol can be made in the laboratory by the hydration of cyclohexene using

concentrated phosphoric acid as a catalyst at low temperature. The cyclohexanol is

purified by distillation.

06.1 Complete the equation for the conversion of cyclohexene to cyclohexanol in

this reaction.

[1 mark]

06.2 Complete the mechanism for this reaction by adding curly arrows in the

relevant places.

[3 marks]

06.3 Concentrated phosphoric acid (H PO ) has a density of 1.69 g cm–3

The concentrated acid contains 85% phosphoric acid and 15% water by mass.

Calculate the amount, in mol, of phosphoric acid in 6.0 cm3 of

concentrated phosphoric acid.

[2 marks]

Amount of phosphoric acid mol

A student sets up the apparatus shown in Figure 2 to purify the cyclohexanol by

distillation. Suitable clamps are used to hold the apparatus firmly in place.

Figure 2

06.4 Explain why the condenser in Figure 2 is connected so that water enters at the

bottom and not at the top.

[2 marks]

06.5 The flask heated in Figure 2 contains anti-bumping granules.

State why these are used.

[1 mark]

06.6 Suggest why the flask in Figure 2 is heated with an electric heater, rather than a

Bunsen burner.

[1 mark]

06.7 State why the apparatus set up in Figure 2 is dangerous.

State how this problem could be solved.

[2 marks]

Why the apparatus is dangerous

How to solve the problem

06.8 The cyclohexanol can be dehydrated to re-form cyclohexene by heating with

concentrated phosphoric acid.

Name the mechanism for this reaction.

[1 mark]

Cyclohexanol biofuel can be made from waste biomass materials such as

rice and straw.

Cyclohexanol biofuel can be mixed with diesel and used as fuel in cars.

06.9 Give an equation for the complete combustion of cyclohexanol (C6H11OH).

[1 mark]

06.10 The use of cyclohexanol biofuel mixed with diesel in cars is not carbon-neutral.

State the meaning of the term carbon-neutral.

Give a reason why the use of this mixture as a fuel is not carbon-neutral.

[2 marks]

Carbon-neutral meaning

Why the fuel is not carbon-neutral

Mark scheme

Show the mark scheme Mark scheme for Question 06: 06.1 gives cyclohexene + H2O -> cyclohexanol (1 mark); 06.2 gives 3 marks for three curly arrows (from double bond to H+, lone pair on oxygen to carbocation, and O-H bond to O+); 06.3 gives mass = 10.14 g and amount = 0.0879 mol (2 marks); 06.4 awards 2 marks for ensuring the condenser fills with water and stays cool; 06.5 awards 1 mark for producing smaller bubbles/preventing large bubbles; 06.6 awards 1 mark for cyclohexanol/mixture being flammable; 06.7 awards 2 marks for stating the system is closed/sealed leading to pressure build-up, and adding a vent/opening; 06.8 awards 1 mark for elimination; 06.9 gives C6H11OH + 8.5 O2 -> 6 CO2 + 6 H2O (1 mark); 06.10 awards 2 marks for no net carbon dioxide emissions into the atmosphere, and noting diesel is a fossil fuel or fossil fuels are burned during processing/transport.

Question Marking guidance Additional Comments/Guidelines Mark

Do not allow equations with H PO or H+ on both

sides 1

06.1

Ignore any acids (or attempt at formula of an acid) (1 x AO2)

on the arrow.

M1 curly arrow from C=C to H+ Mark each of the three stages independently. Any

extra curly arrows within each of the three steps of

M2 curly arrow from lone pair on O to positive C atom the mechanism would contradict the correct arrow

within that step.

M3 curly arrow from an O–H bond to O

06.2

(3 x AO2)

– AS CHEMISTRY – 7404/2 –

M1 Mass of concentrated phosphoric acid = 6.0 × 1.69 (= 10.14 g) 0.10(3) scores 1 mark (at least 2 sf) for not using

M1 × 0.85 85%

M2 Amount of H3PO4 = = 0.0879 mol (at least 2sf) 2

06.3 98.0 Allow 1 mark for = 6.0 x 1.69 x 0.85 (= 8.619 g)

(2 x AO2)

6.0 × 1.69 x 0.85 8.619

Allow 1 mark for = =

incorrect 𝑀𝑟 incorrect 𝑀𝑟

M1 idea of ensuring the condenser fills with water M1 allow idea of no air bubbles

06.4 M2 idea that condenser is cool(er) or ensuring (more) vapour M2 not water vapour; ignore cyclohexene

(2 x AO1)

condenses

06.5 to produce smaller bubbles / prevent the formation of large bubbles – AS CHEMISTRY – 7404/2 –

(1 x AO1)

06.6 as the mixture / cyclohexanol is flammable Igno0re to control temperature

(1 x AO3)

M1 System is closed / sealed M1 allow build-up of pressure 2

06.7

M2 idea of vent or opening on or near the collection flask (2 x AO3)

Allow acid catalysed elimination

– AS CHEMISTRY – 7404/2 – 1

06.8 elimination Ignore dehydration

(1 x AO1)

Not acid-based elimination

Allow multiples / fractions

06.9 C6H11OH + 8 O2 ⟶ 6CO2 + 6H2O Allow C6H12O

2 (1 x AO2)

Ignore state symbols

M1 (A carbon-neutral fuel results in) no net emissions of carbon

dioxide to the atmosphere/air

06.10 M2 (Extra CO2 will be emitted) because of use of fossil fuels in (1 x AO1,

processing / transport 1 x AO2)

OR contains diesel which is non-renewable/fossil fuel/not biofuel

How to answer it

Cyclohexene Hydration, Distillation & Biofuels Study Guide

📌 What this question tests

This question assesses practical and theoretical organic chemistry: writing addition and combustion equations, drawing an electrophilic addition mechanism (hydration of an alkene), calculating amounts in moles using density and percentage purity, evaluating laboratory apparatus for distillation (including practical safety, boiling control, and condenser efficiency), identifying elimination mechanisms, and defining/evaluating "carbon-neutral" fuels.

Question 06.1: Hydration Equation

Overall equation for the formation of cyclohexanol [1 Mark]

✅ Correct Answer

Add + H₂O to the reactant side:

Cyclohexene + H₂O → Cyclohexanol

❌ Common Errors

  • Writing + H₃PO₄ or + H⁺ on the reactant side. Phosphoric acid is a catalyst, not a stoichiometric reagent.
  • Writing H₃PO₄ or H⁺ on both sides of the equation.
Mark scheme: 1 mark for + H₂O on left-hand side. Acids above or below the reaction arrow are ignored.

Question 06.2: Electrophilic Addition Mechanism

Adding curly arrows to show the hydration of cyclohexene [3 Marks]

✅ Correct Arrows (3 Marks)

  • Arrow 1 (M1): From the C=C double bond to the H⁺ ion.
  • Arrow 2 (M2): From the lone pair on the oxygen atom of :OH₂ to the positively charged carbon atom (carbocation) on the ring.
  • Arrow 3 (M3): From one of the O–H single bonds onto the O⁺ atom of the protonated intermediate.

🧠 Exam Technique: Curly Arrow Rules

  • Start precisely: Arrows must begin either from the centre of a bond or directly from a lone pair of electrons.
  • Point precisely: The arrowhead must point directly at the atom receiving electrons.
  • Never draw arrows pointing away from a positive charge; electrons move toward positive or electron-deficient centres!
Mark scheme: Each arrow scored independently (3 × AO2). Any extra conflicting arrows in a step will cancel the mark for that step.

Question 06.3: Multi-Step Density & Purity Calculation

Calculate amount (in mol) of H₃PO₄ in 6.0 cm³ of concentrated acid [2 Marks]

📐 Step-by-Step Calculation

Step 1: Calculate total mass of solution

Mass = Volume × Density = 6.0 cm³ × 1.69 g cm⁻³ = 10.14 g

Step 2: Calculate mass of pure H₃PO₄ (85% by mass)

Mass of pure acid = 10.14 g × 0.85 = 8.619 g

Step 3: Calculate Mr of H₃PO₄

Mr = (3 × 1.0) + 31.0 + (4 × 16.0) = 98.0 g mol⁻¹

Step 4: Calculate moles

Moles = 8.619 / 98.0 = 0.087948... mol

Final Answer: 0.088 mol (or 0.0879 mol, at least 2 sig figs)

❌ Common Errors & Examiner Traps

  • Forgetting the 85% purity: Dividing 10.14 directly by 98.0 gives 0.103 mol (loses M2, scores only 1 mark).
  • Incorrect Mr: Ensure correct atomic masses from the Periodic Table (H = 1.0, P = 31.0, O = 16.0 → 98.0). If Mr is wrong, error carried forward (ECF) allows 1 mark.
  • Premature rounding: Keep intermediate values in your calculator memory to avoid rounding errors in the final answer.
Mark scheme: M1: Mass of concentrated acid = 6.0 × 1.69 (= 10.14 g) OR calculating mass of pure acid = 8.619 g. M2: 0.0879 mol (allow 0.088 mol, at least 2 sf).

Question 06.4: Condenser Setup

Why water enters at the bottom and leaves at the top [2 Marks]

✅ Correct Answer

  • M1: To ensure the outer jacket of the condenser fills completely with water (prevents air bubbles / air pockets from forming).
  • M2: To keep the condenser cooler / ensure more efficient cooling so that vapour condenses effectively.

❌ Common Misconceptions

  • Saying "to condense water vapour" – the liquid being purified is cyclohexanol, not water!
  • Only stating "it cools the vapour" without explaining that filling from the bottom prevents airlocks and fills the entire jacket.
Mark scheme: M1: ensures condenser fills completely / no air bubbles. M2: condenser is cool(er) / ensures (more) vapour condenses.

Question 06.5: Anti-Bumping Granules

Purpose of adding anti-bumping granules [1 Mark]

✅ Correct Answer

To produce smaller bubbles / prevent the formation of large bubbles (or promote smooth and even boiling).

❌ Avoid Vague Wording

  • Do not just write "to stop bumping" – explain the physical action: producing small bubbles / preventing vigorous uneven boiling.
  • Do not say "to lower the boiling point" or "to speed up the reaction" (anti-bumping granules are chemically inert).
Mark scheme: 1 mark for: to produce smaller bubbles / prevent the formation of large bubbles.

Question 06.6: Electric Heating Mantle vs Bunsen Burner

Why use an electric heater rather than an open flame? [1 Mark]

✅ Correct Answer

The organic mixture / cyclohexanol is flammable.

❌ Insufficient Answers

  • "To control the temperature better" is ignored by the mark scheme because the primary laboratory safety hazard is flammability near a naked flame.
Mark scheme: 1 mark for identifying that the mixture / cyclohexanol is flammable. Ignore "to control temperature".

Question 06.7: Practical Apparatus Safety

Identify the danger in Figure 2 and how to fix it [2 Marks]

✅ Correct Answers

Why dangerous (M1): The system is completely closed / sealed (which leads to a hazardous build-up of pressure inside glassware).

How to solve (M2): Provide a vent / opening on or near the collection flask (or do not seal the delivery adapter into the receiving flask).

🧠 Exam Technique: Apparatus Spotting

Always examine joints carefully in distillation diagrams:

  • A sealed joint at the collection vessel forms a rigid, airtight system. As gases are heated, pressure rises: pV = nRT .
  • Heating a closed system can cause catastrophic apparatus explosion!
Mark scheme: M1: System is closed / sealed (allow "build-up of pressure"). M2: Provide a vent / opening on or near the collection flask.

Question 06.8: Dehydration Mechanism Name

Name the mechanism for converting cyclohexanol back to cyclohexene [1 Mark]

✅ Correct Answer

Elimination (or acid-catalysed elimination)

❌ Common Errors

  • Dehydration: This describes the reaction type (loss of water), not the formal IUPAC reaction mechanism name. The mark scheme explicitly states "ignore dehydration".
  • Do not write "electrophilic elimination" or "nucleophilic elimination". Simply write elimination.
Mark scheme: 1 mark for "elimination". Allow "acid catalysed elimination". Ignore "dehydration". Reject "acid-based elimination".

Question 06.9: Combustion Equation

Complete combustion of cyclohexanol (C₆H₁₁OH) [1 Mark]

✅ Balanced Chemical Equation

C₆H₁₁OH + 8½ O₂ → 6 CO₂ + 6 H₂O

Or using whole integer coefficients:

2 C₆H₁₁OH + 17 O₂ → 12 CO₂ + 12 H₂O

🧠 Balancing Tip: Don't forget the Oxygen in the Alcohol!

  • 6 Carbons → 6 CO₂ (needs 12 'O' atoms)
  • 12 Hydrogens (11 + 1) → 6 H₂O (needs 6 'O' atoms)
  • Total O needed on right = 12 + 6 = 18 'O' atoms
  • There is already 1 'O' in C₆H₁₁OH, so you only need 17 more 'O' atoms from oxygen gas → 8.5 O₂ (or 17/2 O₂ ).
Mark scheme: 1 mark for balanced equation. Fractions or multiples allowed. State symbols not required. Formula may be written as C₆H₁₂O.

Question 06.10: Carbon-Neutrality Analysis

Definition and application to a biofuel/diesel mixture [2 Marks]

💡 Carbon-Neutral Meaning (M1)

An activity/fuel that results in no net emissions of carbon dioxide to the atmosphere/air (the CO₂ released during burning equals the CO₂ absorbed during growth of the plant material).

✅ Why This Mixture is NOT Carbon-Neutral (M2)

Any one valid point:

  • It contains diesel, which is a fossil fuel / non-renewable and releases locked-up ancient carbon as net CO₂.
  • Fossil fuels are burned / energy is consumed during the transportation, harvesting, or industrial processing of the biomass.
Mark scheme: M1: No net emissions of carbon dioxide to the atmosphere/air. M2: Extra CO₂ emitted due to use of fossil fuels in processing/transport OR contains diesel which is a fossil fuel / non-renewable.

Topics

Organic Chemistry · Physical Chemistry · Required Practicals · 3.1.2 Amount of Substance · 3.3.4 Alkenes · 3.3.5 Alcohols · Required Practical 5: Distillation of a product from a reaction

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