JEE Main Chemistry question

Correct order of dehydration of a series of benzylic secondary/tertiary alcohols with varying ring substitution (methyl-substituted vs nitro-substituted benzylic alcohols) is

(A)Tertiary benzylic (with two ring methyls) > secondary benzylic (with one ring methyl) > secondary benzylic (unsubstituted ring) > secondary benzylic (with ring )Correct
(B)Reverse of (a)
(C)Nitro-substituted fastest
(D)All equal

Answer: (A)

Solution

Dehydration ease (via carbocation formation) is increased by electron-donating ring substituents (like , which stabilise the benzylic cation by hyperconjugation/induction) and decreased by electron-withdrawing substituents

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Question ID VK-148583