The cyclic imide shown is treated with Br2 and excess aqueous NaOH and then acidified gently. Which structure is the product?

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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc246

The cyclic imide shown is treated with $Br X_{2}$ and excess aqueous $NaOH$ and then acidified gently. Which structure is the product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The compound shown is phthalimide. Alkaline hydrolysis opens the imide to the phthalamate (an amide with a carboxylate), whose amide group undergoes the Hofmann rearrangement. The product is 2-aminobenzoic acid (anthranilic acid), which keeps the carboxyl group and is not decarboxylated.

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The cyclic imide shown is treated with BrX2​ and excess aqueous NaOH and then acidified gently. Which structure is the product?

Answer: D

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The cyclic imide shown is treated with $Br X_{2}$ and excess aqueous $NaOH$ and then acidified gently. Which structure is the product?