*o*-Toluic acid on reaction with Br_2 + Fe gives [Manipal 2010]

JEE Main Chemistry question

*o*-Toluic acid on reaction with Br + Fe gives [Manipal 2010]

(A)a ring-brominated product with Br *para* to –CH and *meta* to –COOH
(B)a side-chain brominated product at the benzylic CH (ionic bromination of the ring methyl does not occur under Br/Fe)
(C)a ring-brominated product with Br *ortho* to –COOH and *meta* to –CHCorrect
(D)a di-brominated product at both *ortho* positions to –CH

Answer: (C)

Solution

Br/Fe is an electrophilic (ionic) ring-bromination condition, not a radical side-chain condition. In *o*-toluic acid, the methyl group (weak *o*/*p*-director) and the carboxylic acid group

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Question ID VK-142289