Solved: The Mannich reaction of a ketone, an amine, and an aldehyde is one of the few

Chapter 23, Problem 23.64

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The Mannich reaction of a ketone, an amine, and an aldehyde is one of the few three-component reactions in organic chemistry. Cyclohexanone, for example, reacts with dimethylamine and acetaldehyde to yield an amino ketone. The reaction takes place in two steps, both of which are typical carbonyl-group reactions. (CH3)2NH CH3CHO H+ catalyst + + CH3 O O N(CH3)2(a) The first step is reaction between the aldehyde and the amine to yieldan intermediate iminium ion (R2CPNR21) plus water. Propose a mechanism,and show the structure of the intermediate iminium ion.(b) The second step is reaction between the iminium ion intermediate andthe ketone to yield the final product. Propose a mechanism.

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