Question

The heating of phenyl methyl ether with $HI$ produces:

• A. iodobenzene
• B. phenol
• C. benzene
• D. ethyl chloride

Answer 1

The correct option is B phenol

Start with protonating the oxygen of the ether (by the acid of course):

$I^{-}$ can only ever attack the carbon of the methyl group. The other carbon which is part of the benzene ring is not
at all approachable because the delocalized $\pi$ electron cloud blocks and prevents nucleophiles from attacking the
$s{p}^2$ carbon.