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Compound (A), C8H9Br, gives a white precipitate when warmed with alcoholic AgNO3. Oxidation of (A) gives an acid (B), C8H6O4. (B) easily forms anhydride on heating. Identify the compound (A).

1. p-bromobenzyl bromide with a methyl group on the ring
2. o-bromobenzyl bromide with a methyl group on the ring
3. m-bromobenzyl bromide with a methyl group on the ring
4. bromotoluene with an ethyl group on the ring

Correct answer: o-bromobenzyl bromide with a methyl group on the ring

Solution

The correct option is o-bromobenzyl bromide with a methyl group on the ring because the presence of the ortho-bromine and the methyl group allows for the formation of a carboxylic acid upon oxidation, which can subsequently form an anhydride, consistent with the properties described.

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