JEE Main Chemistry question

o-Toluic acid on reaction with Br₂ + Fe gives

(A)A ring-brominated product with Br para to the methyl, COOH retainedCorrect
(B)A side-chain-brominated product (benzylic CH₂Br), COOH retained
(C)A ring-brominated product with Br para to the methyl and a second Br on the methyl-bearing carbon
(D)A ring-brominated product with Br ortho to the methyl (different regiochemistry)

Answer: (A)

Solution

Br₂/Fe is an ionic (electrophilic aromatic substitution) bromination condition, not a radical (benzylic) one — it brominates the ring, not the side chain. In o-toluic acid (2-methylbenzoic acid), the methyl group is a weak o/p-director while the –COOH group is a

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Question ID VK-149536