Reaction of a ketone with hydroxylamine yields which type of compound?

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Multiple Choice

Reaction of a ketone with hydroxylamine yields which type of compound?

When a carbonyl compound reacts with hydroxylamine, you form an oxime. The exact name depends on the type of carbonyl: aldehydes give aldoximes, ketones give ketoximes. The reaction mechanism involves the lone pair on the hydroxylamine nitrogen attacking the carbonyl carbon, forming a hemiaminal intermediate, which then loses water to yield the C=N–OH group. Since a ketone has two alkyl/aryl groups on the carbon, the product is specifically a ketoxime, with the structure R2C=NOH. Hydrazine would give a hydrazone, and a primary amine would give an imine, not an oxime.

When a carbonyl compound reacts with hydroxylamine, you form an oxime. The exact name depends on the type of carbonyl: aldehydes give aldoximes, ketones give ketoximes. The reaction mechanism involves the lone pair on the hydroxylamine nitrogen attacking the carbonyl carbon, forming a hemiaminal intermediate, which then loses water to yield the C=N–OH group. Since a ketone has two alkyl/aryl groups on the carbon, the product is specifically a ketoxime, with the structure R2C=NOH. Hydrazine would give a hydrazone, and a primary amine would give an imine, not an oxime.

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