Consider the following reaction.C_6H_5-O-CH_2 | vedclass

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Question

(D) The reaction of an ether with $HI$ involves the protonation of the ether oxygen atom, followed by a nucleophilic attack by the iodide ion $(I^-)$.

Vedclass · Accepted Answer

Statement $I$ is false but Statement $II$ is true

Vedclass · Answer

(D) The reaction of an ether with $HI$ involves the protonation of the ether oxygen atom, followed by a nucleophilic attack by the iodide ion $(I^-)$.In the given ether, benzyl phenyl ether $(C_6H_5-O-CH_2-C_6H_5)$, the oxygen atom is attached to a phenyl group and a benzyl group.The cleavage occurs such that the more stable carbocation is formed. The benzyl carbocation $(C_6H_5CH_2^+)$ is resonance-stabilized and more stable than the phenyl carbocation.Therefore, the $C-O$ bond on the benzylic side is cleaved, leading to the formation of benzyl iodide $(C_6H_5CH_2I)$ and phenol $(C_6H_5OH)$.Statement $I$ claims the products are benzyl alcohol and iodobenzene, which is incorrect.Statement $II$ correctly states that the $-O-CH_2-$ bond is cleaved.Thus, Statement $I$ is false and Statement $II$ is true.

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