Question

Anisole is treated with $HI.$ Products obtained are:-

• A. Ethyl alcohol and phenyl iodide
• B. methyl alcohol and benzene
• C. methyl iodide & phenyl iodide
• D. methyl iodide & phenol

Answer 1

The correct option is D methyl iodide & phenol

In case of anisole, methylphenyl oxonium ion, is formed by protonation of ether. The bond between $O–C{H}_3$ is weaker than the bond between $O–C_6{H}_5$ because the carbon of phenyl group is $s{p}^2$ hybridised and there is a partial double bond character. Therefore the attack by I– ion breaks $O–C{H}_3$ bond to form $C{H}_{3}I$. Phenols do not react further to give halides because the $s{p}^2$ hybridised carbon of phenol cannot undergo nucleophilic substitution reaction needed for conversion to the halide.