Edexcel A-Level Chemistry AS Paper 2, June 2016: Question 1

8 marks · Medium difficulty · Short Open Response

Identify alkane nomenclature, structural isomers, reforming equations, and free-radical substitution mechanisms involving initiation, propagation, and termination steps.

Practise this question

Question

A multi-part chemistry exam question about alkanes. Part (a) shows a skeletal formula of a branched alkane and asks for its name from four multiple-choice options. Part (b) asks for the number of structural isomers of C5H12 from four options. Part (c) requires writing a reforming equation for heptane into cycloheptane with skeletal formulae. Part (d) covers the free-radical substitution of ethane with chlorine, including a multiple-choice question on bond fission type, writing propagation steps, and explaining the formation of butane in the termination step.
Question text

1 Alkanes are a homologous series of hydrocarbons.

(a) What is the name of this compound?

(1)

A 1,1,2-trimethylpentane

B 2,3-dimethylhexane

C 4,5-dimethylhexane

D 4,5,5-trimethylpentane

(b) The number of structural isomers with the molecular formula C5H12 is

(1)

A 3

B 4

C 5

D 6

(c) Write the equation for reforming heptane into cycloheptane, showing the skeletal

formulae of the organic molecules.

(2)

(d) Ethane reacts with chlorine in the presence of ultraviolet light to form a mixture

of products.

(i) In the initiation step, chlorine molecules are converted into radicals.

Cl2 o 2Cl∙

Identify the type of bond broken and the type of bond fission occurring in this

step.

(1)

Bond broken Bond fission

A ʌ heterolytic

B ı *P49838A0228*heterolytic

C ʌ homolytic

D ı homolytic

(ii) Write the propagation steps to show the formation of C2H5Cl.

(2)

(iii) State how some butane, C4H10, is formed in the reaction.

(1)

(Total for Question 1 = 8 marks)

Mark scheme

Show the mark scheme The mark scheme provides the answers and guidance for all parts of Question 1. Part (a) is B (2,3-dimethylhexane). Part (b) is A (3). Part (c) awards 2 marks for the correct skeletal equation of heptane reforming into cycloheptane and hydrogen. Part (d)(i) is D (sigma, homolytic). Part (d)(ii) awards 2 marks for the two propagation equations showing the formation of C2H5Cl. Part (d)(iii) awards 1 mark for stating that two ethyl radicals react together during termination.

How to answer it

Alkanes & Free Radical Substitution Study Guide

What this question tests

This AS Chemistry exam question assesses your understanding of alkane nomenclature, structural isomerism, reforming reactions, and free radical substitution mechanisms (specifically initiation, propagation, and termination steps, including bond fission).

Part (a) — IUPAC Nomenclature

Naming Alkanes from Skeletal Formulae

✅ Correct Answer

B (2,3-dimethylhexane)

💡 Key Knowledge

  • Find the longest continuous carbon chain (6 carbons = hexane).
  • Number the chain from the end that gives substituents the lowest possible locants (from right to left gives methyl groups at positions 2 and 3 rather than 4 and 5).
  • Combine identical substituents using the prefix 'di-'.

❌ Common Errors

Choosing a wrong numbering direction or miscounting the longest carbon chain, leading to incorrect locants like 4,5-dimethylhexane.

Mark: 1 mark
Part (b) — Isomerism

Structural Isomers of C₅H₁₂

✅ Correct Answer

A (3)

💡 Key Knowledge

Pentane has 3 structural isomers: pentane (straight chain), 2-methylbutane (branched), and 2,2-dimethylpropane (double branched).

🧠 Exam Technique

Systematically draw straight chains first, then shorten the main chain by one carbon to use as a methyl branch, checking for duplicates.

Mark: 1 mark
Part (c) — Reforming Equations

Reforming Heptane into Cycloheptane

✅ Correct Answer

Skeletal formula of heptane (7-carbon zig-zag chain) reacting to form the skeletal formula of cycloheptane (7-membered ring) plus H₂ .

💡 Key Knowledge

Reforming involves converting straight-chain alkanes into cyclic alkanes and hydrogen gas. You must use clear skeletal formulae for the organic structures as requested.

❌ Common Errors

Using molecular, structural, or displayed formulae instead of skeletal drawings for the organic molecules. Max 1 mark can be awarded if extra reactants/products (like excess hydrogen) are included incorrectly.

Marks: 2 marks (1 for correct skeletal structures of heptane and cycloheptane, 1 for the formula of hydrogen H₂ )
Part (d)(i) — Bond Fission

Initiation Step Characteristics

✅ Correct Answer

D ( σ bond broken, homolytic fission)

💡 Key Knowledge

Single covalent bonds are σ (sigma) bonds. Homolytic fission occurs when the bonded pair of electrons is split equally between the two atoms, forming two radicals.

❌ Common Errors

Confusing homolytic fission (radical formation, equal split) with heterolytic fission (unequal split forming ions).

Mark: 1 mark
Part (d)(ii) — Mechanism

Propagation Steps for Chloroethane Formation

✅ Correct Answer

Step 1: C₂H₆ + Cl• → C₂H₅• + HCl
Step 2: C₂H₅• + Cl₂ → C₂H₅Cl + Cl•

💡 Key Knowledge

Propagation steps always feature a molecule and a radical reacting to form a new molecule and a new radical. Notice how the chlorine radical ( Cl• ) is regenerated in step 2.

🧠 Exam Technique

Ensure radical dots ( • ) are clearly positioned on the correct species. Equations can be written in either order, but both are required for full marks.

❌ Common Errors

Forgetting to include radical dots or mixing up propagation steps with initiation or termination steps. Missing radical dots are usually penalised once across the whole script.

Marks: 2 marks (1 mark per correct propagation equation)
Part (d)(iii) — Side Reactions

Formation of Butane Byproduct

✅ Correct Answer

Two ethyl radicals react together: C₂H₅• + C₂H₅• → C₄H₁₀ (or described in words as two ethyl radicals combining).

💡 Key Knowledge

Trace amounts of longer-chain alkanes like butane form during free radical substitution via a termination step where two alkyl radicals collide and bond.

❌ Common Errors

Attempting to write initiation, propagation, or ionic equations instead of focusing on the radical combination step. Do not use molecules or ions as reactants here.

Mark: 1 mark

Topics

Organic Chemistry · Topic 6: Organic Chemistry I

Question and mark scheme from the Edexcel A-Level Chemistry examination, AS Paper 2, June 2016. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.