JEE Advanced levelSingle correct optionDifficulty 3 of 3si214
Benzene is acylated with CHX3COCl and anhydrous AlClX3 to give A. A is reduced with Zn-Hg/conc. HCl to give B. B is heated with alkaline KMnOX4 and then acidified to give C. C is treated with BrX2/FeBrX3 to give D. D is
A4-bromobenzoic acid
B3-bromobenzoic acid
C2-bromobenzoic acid
Dbenzoyl bromide
Answer: B
A is acetophenone, B is ethylbenzene (Clemmensen), C is benzoic acid (any alkyl side chain with a benzylic H is oxidised to COOH). The carboxyl group is a meta director, so bromination gives 3-bromobenzoic acid.