Section 18.6. Reaction with secondary nucleophilic nitrogen.
Secondary amines react with the carbonyl group of aldehydes and ketones to form a tetrahedral complex which has no hydrogen on the nitrogen. When water is eliminated from this complex, a C,N pi bond cannot form, and instead a C,C pi bond is formed, giving an enamine. Enamines have significant importance in synthesis as the C,C pi bond is activated as a nucleophile at the carbon away from the nitrogen.
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