Edexcel A-Level Chemistry Paper 2, June 2023: Question 2

6 marks · Medium difficulty · Short Open Response

Answer questions related to the properties, reactions, combustion, conversion, infrared spectroscopy, carbon-13 NMR, and oxidation half-equations of various alcohols.

Practise this question

Question

A structured examination question about alcohols consisting of five parts labeled (a) through (e). Part (a) is a multiple-choice question on whether ethanol from fermentation is a biofuel and renewable or non-renewable. Part (b) asks for the equation for complete combustion of methanol without state symbols. Part (c) asks for the reagents needed to convert propan-1-ol into 1-iodopropane. Part (d) has two parts: (i) a multiple-choice question on wavenumber ranges for propan-2-ol in an infrared spectrum, and (ii) stating the number of peaks in the 13C NMR spectrum of propan-2-ol. Part (e) gives an overall oxidation equation of ethanol and asks to deduce the half-equation for the oxidation of ethanol to ethanoic acid.
Question text

2 This question is about alcohols.

(a) Ethanol is a fuel and can be made by either the fermentation of carbohydrates or

the hydration of ethene.

How is the ethanol formed by the fermentation of carbohydrates classified?

(1)

A a biofuel and non-renewable

B a biofuel and renewable

C a fossil fuel and non-renewable

D a fossil fuel and renewable

(b) Write the equation for the complete combustion of methanol.

State symbols are not required.

(1)

(c) Identify, by name or formula, the reagent(s) needed to convert propan-1-ol

into 1-iodopropane.

(1)

(d) A sample of pure propan-2-ol is analysed using infrared and

13C NMR spectroscopy.

(i) Which of these sets of wavenumber ranges, in cm–1, will be seen in the

infrared spectrum of propan-2-ol?

(1)

A 1485 – 1365, 2962 – 2853 and 3300 – 2500

B 1485 – 1365, 2962 – 2853 and 3750 – 3200

C 1669 – 1645, 2962 – 2853 and 3750 – 3200

D 1740 – 1720, 3300 – 2500 and 3750 – 3200

(ii) State the number of peaks in the 13C NMR spectrum of propan-2-ol.

(1)

(e) The equation for the oxidation of ethanol by acidified dichromate(VI) ions

is shown.

4 3CH CH OH + 2Cr O2– + 16H+ → 3CH COOH + 4Cr3+ + 11H O

32 2 7 3 2

Deduce the half-equation for the oxidation of ethanol to ethanoic*P71913A0428*acid.

State symbols are not required.

(1)

(Total for Question 2 = 6 marks)

Mark scheme

Show the mark scheme The mark scheme provides answers and guidance for all parts of Question 2. Part (a) shows answer B is correct. Part (b) lists accepted balanced equations for methanol combustion. Part (c) accepts red phosphorus and iodine or phosphorus(III) iodide with additional acceptable combinations. Part (d)(i) shows answer B is correct. Part (d)(ii) gives 2 as the number of peaks. Part (e) shows the accepted half-equation for the oxidation of ethanol to ethanoic acid with electrons and hydrogen ions.

Question Answer Mark

number

2(a) (1)

The only correct answer is B (a biofuel and renewable)

A is incorrect because ethanol is renewable using the fermentation process

C is incorrect because ethanol is made from plants and is renewable using the fermentation process

D is incorrect because ethanol is made from plants

Question

Answer Additional Guidance Mark

Number

2(b) Example of equation (1)

• balanced equation

CH3OH + 1½O2 → CO2 + 2H2O

or

2CH3OH + 3O2 → 2CO2 + 4H2O

Allow fractions e.g. 3/2 O2

Allow CH4O for methanol

Ignore state symbols

Question

Answer Additional Guidance Mark

Number

2(c) Allow name or formula but if both are given both (1)

must be correct.

• (red) phosphorus and iodine / P or P4 and I2

or Allow potassium or sodium iodide / KI or NaI and

phosphorus(III) iodide / PI3 phosphoric(V) acid / H3PO4

Allow white phosphorus and iodine

Allow hydrogen iodide / HI

Allow red phosphorus and PI3

Ignore solvent

Do not award phosphorus(V) iodide / PI5

Do not award KI and /or H2SO4

number

2(d)(i) −1 (1)

The only correct answer is B (1485 – 1365, 2962 – 2853 and 3750 − 3200 cm )

A is incorrect because 3300 − 2500 cm−1 is for an O-H in a carboxylic acid

C is incorrect because 1669 – 1645 cm−1 for C=C in an alkene

D is incorrect because 1740 – 1720 cm−1 is for C-O in an aldehyde and 3300 − 2500 cm−1 is for an O-H in a carboxylic acid

Question

Answer Additional Guidance Mark

Number

2(d)(ii) (1)

• 2 / two

Question

Answer Additional Guidance Mark

Number

2(e) Example of half-equation (1)

• half-equation

CH CH OH + H O → CH COOH + 4H+ + 4e−

32 2 3

Allow multiples

Allow −4e− on left hand side of equation

Ignore missing charge on electron

Ignore state symbols

(Total for Question 2 = 6 marks)

How to answer it

Properties, Reactions, and Analysis of Alcohols

What this question tests

This question assesses core organic chemistry topics relating to alcohols: classifications of biofuels, writing complete combustion equations, halogenoalkane synthesis reagents, infrared spectroscopy absorption interpretation, carbon-13 (¹³C) NMR environments, and constructing redox half-equations in acidic conditions.

Part (a) — Biofuel Classification

Classifying Ethanol from Fermentation

✅ Correct Answer

B — a biofuel and renewable

💡 Key Knowledge

Fuels derived from biomass (plants/crops) are classified as biofuels. Because crops can be regrown continually over a short time frame, the fuel is considered renewable.

❌ Common Errors

Choosing option A or C. Students sometimes confuse fermentation products with fossil fuels, or forget that plant-derived fuels are naturally renewable.

Mark: 1 mark
Part (b) — Combustion Equation

Complete Combustion of Methanol

✅ Correct Answer

CH₃OH + 1.5O₂ → CO₂ + 2H₂O

(Or multiplied across by 2 to use whole numbers: 2CH₃OH + 3O₂ → 2CO₂ + 4H₂O )

🧠 Exam Technique

Always balance carbon first, hydrogen second, and leave oxygen (especially O₂) until the very end. Fractions like 1.5 or 3/2 are fully accepted by Edexcel.

❌ Common Errors

Forgetting to include oxygen as a reactant, or producing carbon monoxide ( CO ) or carbon ( C ) instead of carbon dioxide ( CO₂ ), which violates the "complete combustion" requirement.

Mark: 1 mark
Part (c) — Halogenoalkane Synthesis

Converting Propan-1-ol to 1-Iodopropane

✅ Correct Answer

Red phosphorus and iodine ( P + I₂ or P₄ + 6I₂ ) OR phosphorus(III) iodide ( PI₃ ).

💡 Key Knowledge

To substitute a hydroxyl group ( -OH ) with an iodine atom, we generate hydrogen iodide in situ using red phosphorus and iodine. Alternatively, pre-formed PI₃ can be used.

❌ Common Errors

Using potassium iodide and sulfuric acid ( KI + H₂SO₄ ). Sulfuric acid oxidises hydrogen iodide to iodine gas, preventing the formation of the desired 1-iodopropane. Also, do not confuse phosphorus(III) iodide ( PI₃ ) with phosphorus(V) iodide ( PI₅ , which does not exist stably).

Mark: 1 mark
Part (d)(i) — Infrared Spectroscopy

Identifying Propan-2-ol IR Absorptions

✅ Correct Answer

B — 1485 – 1365 , 2962 – 2853 and 3750 – 3200 cm⁻¹

💡 Key Knowledge

Propan-2-ol contains an -OH alcohol group (broad peak at 3750 – 3200 cm⁻¹ ), C-H saturated alkane stretches ( 2962 – 2853 cm⁻¹ ), and C-H bending/fingerprint signals ( 1485 – 1365 cm⁻¹ ).

❌ Common Errors

Selecting wavenumber ranges associated with carboxylic acid -OH ( 3300 – 2500 cm⁻¹ ), which appears much broader and extends further down into lower wavenumbers.

Mark: 1 mark
Part (d)(ii) — Carbon-13 NMR

Carbon Environments in Propan-2-ol

✅ Correct Answer

2 / two peaks

💡 Key Knowledge

Propan-2-ol ( CH₃CH(OH)CH₃ ) possesses a plane of symmetry through the central carbon and oxygen atom. Therefore, the two terminal methyl groups are chemically equivalent (1 environment), and the central carbon bonded to the -OH group forms the second unique carbon environment.

❌ Common Errors

Writing 3 peaks by counting every individual carbon atom without accounting for molecular symmetry.

Mark: 1 mark
Part (e) — Redox Half-Equations

Oxidation Half-Equation for Ethanol

✅ Correct Answer

CH₃CH₂OH + H₂O → CH₃COOH + 4H⁺ + 4e⁻

(Accepting valid multiples or electrons on the left as -4e⁻ )

🧠 Exam Technique

Construct half-equations methodically: balance the main organic carbon skeleton first, balance oxygen using water ( H₂O ), balance hydrogen using hydrogen ions ( H⁺ ), and finally balance overall charge using electrons ( e⁻ ).

❌ Common Errors

Failing to balance oxygen atoms correctly (forgetting the H₂O on the reactant side), or getting the electron count wrong due to miscalculating the change in oxidation state of carbon.

Mark: 1 mark

Topics

Organic Chemistry · Physical Chemistry · Topic 6: Organic Chemistry I · Topic 7: Modern Analytical Techniques I · Topic 17: Organic Chemistry II · Topic 5: Formulae, Equations and Amounts of Substance · Topic 3: Redox I · Topic 19: Modern Analytical Techniques II

Question and mark scheme from the Edexcel A-Level Chemistry examination, Paper 2, June 2023. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.