A-LevelChemistryHalogen derivatives9701/12 · Oct/Nov 2019 · Q231 Mark

1-chloro-2-methylbutane reacts with sodium cyanide in ethanol in a nucleophilic substitution reaction. What is the most likely intermediate or transition state in this reaction? [Figure 23.1]

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A[Diagram of a SN2-like transition state for 1-chloro-2-methylbutane where NC and Cl are partially bonded to the primary carbon]

B[Diagram of a SN2-like transition state for a secondary haloalkane where NC and Cl are partially bonded to the central carbon]

C[Diagram of a tertiary carbocation intermediate]

D[Diagram of a secondary carbocation intermediate]

✓ Correct answer

A: [Diagram of a SN2-like transition state for 1-chloro-2-methylbutane where NC and Cl are partially bonded to the primary carbon]

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Topic: Halogen derivatives, A-Level Chemistry (syllabus 9701). Multiple choice, 1 mark.
Source: A-Level Chemistry, Oct/Nov 2019 Paper 1 Variant 2, question 23.

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