The heating of phenyl-methyl ethers with `HI` produces

Options

A. iodobenzene
B. phenol
C. benzene
D. ethyl chlorides

Answer

B

Explanation

In case of alkyl aryl ethers, the products are always phenol and an alkyl halide but never an aryl halide an
Protonation of anisole yields
Since neither phenyl nor methyl forms stable carbocation, the cleavage reaction follows, `S_(n) 2` mechanism. Due to resonance between the lone pair of electrons on the `O` atom and the benzene ring of the phenyl group, the `O - C_(6) H_(5)` bond has partial double bond character and is thus difficult to break. Back attack of `I^(-)` ion excluusively break the weaker `O - CH_(3)` bond:
Phenol does not react `HI` to give iodobenzene as `O - C_(6) H_(5)` has double bond character and is thus difficult to break.