The amide shown is treated with Br2 and aqueous KOH. Which structure is the organic product?

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The amide shown is treated with $Br X_{2}$ and aqueous $KOH$ . Which structure is the organic product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The amide shown is benzamide. Hofmann degradation removes the carbonyl carbon and the phenyl group migrates from carbon to nitrogen through an isocyanate. The product is aniline, not benzylamine, because no carbon is retained between ring and nitrogen.

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The amide shown is treated with BrX2​ and aqueous KOH. Which structure is the organic product?

Answer: C

More questions on Hofmann bromamide and Gabriel synthesis on drawn substrates

The amide shown is treated with $Br X_{2}$ and aqueous $KOH$ . Which structure is the organic product?