Chemistry - ALCOHOL & ETHER Question with Solution | TestHub

Explanation:

To find out the major product of the following reaction.

Concept :

This question is based on simultaneous addition to alkene and ether cleavage by HBr .

Solution:

$\mathrm{HBr}+$ heat cleaves the aryl- ${\mathrm{OCH}}_3$ ether, giving phenol $+{\mathrm{CH}}_3\mathrm{Br}$ (nucleophilic substitution on the alkyl side) by ${\mathrm{S}}_{\mathrm{N}}2$. The $\mathrm{O}-\mathrm{Me}$ bond breaks to form phenol and methyl bromide. The bond between oxygen and the benzene ring does not cleave due to partial double bond character.

The alkene reacts with HBr by Markovnikov addition, giving a secondary bromo compound (CHBr-CH₃ ).