JEE Main Chemistry question

Which of the following undergoes nucleophilic substitution predominantly via the Sₙ1 mechanism?

(A)Benzyl chlorideCorrect
(B)Isopropyl chloride
(C)Chlorobenzene
(D)Ethyl chloride

Answer: (A)

Solution

Although primary, benzyl chloride ionises readily because the resulting benzylic carbocation is strongly resonance-stabilised by the aromatic ring, so Sₙ1 solvolysis is unusually

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Question ID VK-139873