The ketone shown reacts with hydroxylamine in weakly acidic medium. Which structure is the product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

Propanone (acetone) condenses with hydroxylamine, losing water, to give the oxime, with a C=N-OH group in place of C=O. The hydrazone needs hydrazine, and the semicarbazone needs semicarbazide.

Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Acetal, imine and enamine formation

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