Question

Two isomeric compounds $I$ and $II$ are heated with $HBr$. The products obtained are

• A.
• B.
• C.
• D.

Answer 1

Answer: (A)

Reaction $(I)$ takes place via $S_{N}1$ mechanism $OH$ of $C{H}_{2}OH$ group gets substituted by Br because it form stable carbocation and yield 3-(bromo methyl) phenol.
In reaction $(II)$ protonation of ether takes place. 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 partical double bond character.Thus, the reaction yields benzene $1,3$-diol.