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Multiple Choice

Reaction of an aldehyde with hydroxylamine produces which type of compound?

The reaction between an aldehyde and hydroxylamine forms an oxime. Hydroxylamine (NH2–OH) attacks the carbonyl carbon, giving a tetrahedral intermediate, followed by proton transfers and loss of water to produce a C=N–OH bond. The product is an oxime (specifically an aldoxime for an aldehyde). This distinguishes it from hydrazones (formed with hydrazine), imines (formed with ammonia or primary amines), and enamines (formed with secondary amines).

The reaction between an aldehyde and hydroxylamine forms an oxime. Hydroxylamine (NH2–OH) attacks the carbonyl carbon, giving a tetrahedral intermediate, followed by proton transfers and loss of water to produce a C=N–OH bond. The product is an oxime (specifically an aldoxime for an aldehyde). This distinguishes it from hydrazones (formed with hydrazine), imines (formed with ammonia or primary amines), and enamines (formed with secondary amines).