JEE Main Chemistry question

Which one of the following chloro-compounds most readily undergoes solvolysis?

(A) (vinyl chloride)
(B) (chlorobenzene)
(C) (benzyl chloride)Correct
(D) (2-phenylethyl chloride)

Answer: (C)

Solution

Solvolysis proceeds through an -type pathway, so its rate is governed by how stable the carbocation formed on ionisation is. In vinyl chloride and chlorobenzene, the chlorine's lone pair is conjugated into the adjacent system, so the bond is strong and resists ionisation. In 2-phenylethyl chloride,

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Question ID VK-148081