MHT CET 2023 Chemistry question

Identify the product obtained when ethoxybenzene reacts with hot and concentrated HI

(A)Ethyl iodide and PhenolCorrect
(B)Ethyl alcohol and Phenol
(C)Ethyl alcohol and Iodoebnzene
(D)Ethyl iodide and Iodobenzene

Answer: (A)

Solution

With HI an alkyl aryl ether is protonated on oxygen, and iodide then attacks the alkyl carbon by (the aryl C-O bond is not cleaved because of its partial double bond character from resonance and because an carbon cannot undergo ):

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Question ID VK-097420