Q17P - Organic Chemistry (Mcmurry)

Question

What product would you obtain from a base-catalyzed Michael reaction of 3-buten-2-one with each of the following nucleophilic donors?

Step-by-Step Solution

Answer

The addition of a nucleophilic enolate ion donor to the β- carbon of an α, β-unsaturated carbonyl acceptor always gives a conjugate addition product.

Michael reaction

Certain nucleophiles, such as amines, react with α, β-unsaturated aldehydes, and ketones to give a conjugate addition product, rather than a direct addition product, Exactly the same kind of conjugate addiction can occur when a nucleophilic enolate ion reacts with anα, β -unsaturated carbonyl compound—a process known as the Michael reaction.

Michael reactions take place by the addition of a nucleophilic enolate ion donor to the β- carbon of an α, β-unsaturated carbonyl acceptor.

Diagram of Product Obtained