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.
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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
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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).
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.
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.
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.
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).
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.
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.
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.