Anisole on reaction with HI gives phenol and CH3- I as main products and not iodobenzene and CH3OH.

Question

Give reasons for the following:

Anisole on reaction with HI gives phenol and CH₃- I as main products and not iodobenzene and CH₃OH.

Answer 1

Attack of I^-ion on anisole is through S_N² mechanism, which attacks the lesser hindered ^-CH₃ group forming CH₃^-I Also, O=C bond in phenoxide ion is difficult to break due to resonance.