Phenol is treated with NaOH and then CH3I to give X. X is treated with Br2 in ethanoic acid to give Y (major product). Y is then heated with excess hot HI. The aromatic product is

JEE Advanced levelSingle correct optionDifficulty 3 of 3ap216

Phenol is treated with $NaOH$ and then $CH X_{3} I$ to give X. X is treated with $Br X_{2}$ in ethanoic acid to give Y (major product). Y is then heated with excess hot $HI$ . The aromatic product is

Sodium phenoxide with

CH X_{3} I

gives anisole (X). The

- OCH X_{3}

group directs bromine mainly to the para position, giving 4-bromoanisole (Y). Hot

HI

cleaves the

CH X_{3} - O

bond and gives 4-bromophenol with

CH X_{3} I

; the aryl C-Br and aryl C-O bonds are unaffected.