Enamine reaction

Addition with an unsaturated carboxylic acid

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Enamine Reaction Mechanism

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Reaction of an enamine with a saturated carboxylic acid. The lone pair of the nitrogen in the enamine starts the reaction by forming a carbon-nitrogen double bond which breaks the carbon-carbon double bond enabling it to attack the unsaturated carboxylic acid. The extra lone pair on the oxygen then kicks in allowing the double bond to take a hydrogen off the chain thus allowing the enamine to reform, with an additional carboxylic acid group.