JEE Main Chemistry question

Dehydration of the following (four phenol-type ring alcohols with an -OH-bearing benzylic/cyclic side chain, labelled I–IV) in increasing order is

(A)I < II < III < IVCorrect
(B)II < III < IV < I
(C)IV < III < II < I
(D)I < IV < II < III

Answer: (A)

Solution

Dehydration proceeds through a carbocation intermediate, and greater possible conjugation/resonance stabilisation of that carbocation (or of the resulting alkene) makes

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Question ID VK-148650