Chapter 17: Aldehydes and Ketones. Nucleophilic Addition to C=O

Reactions of Primary Amine Derivatives

Reaction type:  Nucleophilic Addition then Elimination

Summary

• Aldehydes and ketones react with a range of primary amine derivatives to give substituted imines.
• The derivatives with ammonia are too unstable to be isolated but can be reduced in situ to amines.
• The mechanism of these type of reactions is shown on the previous page.
• The reaction of 2,4-dinitrophenylhydrazone (2,4-DNP or Brady's reagent) is used as a laboratory test for aldehydes and ketones since the products precipitate as yellow to red solids.

Yellow to red precipitate indicates a positive test result

Related Reactions

• Reactions of Primary Amines

© Dr. Ian Hunt, Department of Chemistry