Anisole reacts with HI to give phenol and methyl iodide and not iodobenzene and methylalchohol

CBSE Class 12 CBSE Class 12 Chemistry
1

Anisole reacts with HI to give phenol and methyl iodide and not iodobenzene and methylalchohol. Give reason and explain the reaction, with mechanism.

2

Anisole on protonation forms methylphenyl oxonium ion.
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The bond between O-CH3 is weaker than the bond between O-C6H5.
This is because of the partial double bond character between oxygen and carbon of the benzene ring.
Hence the I- ion attacks and breaks the O-CH3 bond to give CH3I.
The phenols formed do not react with halides since nucleophilic substitution on aromatic ring is difficult.