Long answer·Standard multi-step (3/5)·No calculator

Difficulty guide

The label describes the problem, not your ability.

1/5 - Foundational

Warm-up setup; checks one basic idea.

2/5 - Routine exam skill

Normal syllabus skill; usually one main rule or interpretation.

3/5 - Standard multi-step

Exam-style problem with multiple steps or a common trap.

4/5 - Hard exam skill

High-end exam problem; combines methods carefully.

5/5 - Challenge

Stretch problem beyond normal exam pressure.

Question

Three compounds are given: A = CH3CH2CH2CH2Cl\mathrm{CH_3CH_2CH_2CH_2Cl}, B = (CH3)3CCl\mathrm{(CH_3)_3CCl} and C = C6H5Cl\mathrm{C_6H_5Cl}. Classify each and compare their expected behaviour towards ordinary nucleophilic substitution.
Total: 3 marks

(a) Classify A, B and C. (1 mark)

(b) Which of A and B is more suitable for an SN2\mathrm{S_N2} pathway, and why? (1 mark)

(c) Why is C much less reactive than A under ordinary nucleophilic substitution conditions? (1 mark)

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cbse-chemistry-12.u6.t6-1.laq.004

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