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What are the key steps in a Stork enamine synthesis?

The Stork enamine synthesis is a valuable method in organic chemistry used to synthesize α,β-unsaturated carbonyl compounds. This synthesis consists of three key steps: enamine formation, Michael addition, and hydrolysis.

In the first step, known as enamine formation, a secondary amine reacts with either a ketone or an aldehyde, resulting in the formation of an enamine. During this reaction, a molecule of water is eliminated. The enamine generated serves as a nucleophile, which means it can donate an electron pair to create a new chemical bond.

The second step involves the Michael addition. In this stage, the enamine produced in the first step reacts with an α,β-unsaturated carbonyl compound. This reaction is classified as a conjugate addition, where the enamine adds across the double bond of the α,β-unsaturated carbonyl compound. The outcome of this reaction is the formation of a new carbon-carbon bond, resulting in a 1,5-dicarbonyl compound.

The final step of the synthesis is hydrolysis. In this stage, the 1,5-dicarbonyl compound is treated with either an acid or a base, which facilitates the conversion into the desired α,β-unsaturated carbonyl compound. This process involves the addition of water and the elimination of the amine that was utilized in the first step.

In summary, the Stork enamine synthesis is a three-step procedure that encompasses enamine formation, Michael addition, and hydrolysis. This method is especially useful in organic chemistry for the efficient generation of α,β-unsaturated carbonyl compounds.

Answered by: Dr. William Davis
IB Chemistry Tutor
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