The nitrile shown is partly hydrolysed to the amide with alkaline hydrogen peroxide, and the amide is then treated with $Br X_{2}$ /aqueous $NaOH$ . Which structure is the final product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

The nitrile shown is benzyl cyanide. Partial hydrolysis gives 2-phenylacetamide; Hofmann degradation then removes the carbonyl carbon, with the benzyl group migrating to nitrogen. The product is benzylamine, with one carbon fewer than the amide.

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The nitrile shown is partly hydrolysed to the amide with alkaline hydrogen peroxide, and the amide is then treated with BrX2​/aqueous NaOH. Which structure is the final product?

Answer: A

More questions on Hofmann bromamide and Gabriel synthesis on drawn substrates

The nitrile shown is partly hydrolysed to the amide with alkaline hydrogen peroxide, and the amide is then treated with $Br X_{2}$ /aqueous $NaOH$ . Which structure is the final product?