The N-substituted imide shown is heated with hydrazine hydrate. Which amine is liberated?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The compound shown is N-propylphthalimide, the intermediate of a Gabriel synthesis. Hydrazinolysis cleaves both C-N bonds of the imide, giving phthalhydrazide and the primary amine bearing the propyl group, propylamine.

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