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  4. Two isomeric compounds I and II are heated with HBr. <img class=img-fluid question-image alt=image src=https://cdn.tardigrade.in/img/question/chemistry/3c32ccaa85eb99fa53ecc83aa5185b48-.png /> The products obtained are

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

KVPYKVPY 2010Organic Chemistry – Some Basic Principles and Techniques

Solution:

image
Reaction $(I)$ takes place via $S_N1$ mechanism $OH$ of $CH_2OH$ 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 $O —CH_3$ is weaker than the bond between $O—C_6H_5$ because the carbon of phenyl group is $sp^2$-hybridised and there is a partical double bond character.Thus, the reaction yields benzene $1, 3$-diol.