Phenyl methyl ether reacts with HI to give phenol and methyl iodide and not iodobenzene and methyl alcohol. Explain,

Explanation

When phenyl methyl ether treated with HI then products are phenol and methyl iodide. As protonation of anisole gives methyl phenyl oxonium ion `C_(6)H_(5)-underset(H)underset(|)overset(+)O-CH_(3)` In this ion bond between `O-CH_(3)` is weaker than the bond between `O - C_(6)H_(5)` (partial double bond character). So attack by `l^(-)` ion breaks weaker `O-CH_(3)` bond forming `CH_(3)-I` and phenol. Phenol thus formed not reacts further to form aryl halides as `sp^(2)` hybridized carbon-atom of phenol do not undergo nucleophilic substitution reaction to form corresponding aryl halides.