Q66E - Organic Chemistry (Mcmurry)

Question

The following reaction involves two successive intramolecular Michael reactions. Write both steps, and show their mechanisms.

Step-by-Step Solution

Answer

The Intramolecular Michael reaction generally occurs in those compounds which have more than one functional group which are able to stabilize the carbonyl compounds.

In this reaction addition of nucleophile, is often referred to as donor to an acceptor.

Formation of an enolate anion and first Michael addition

Second Michael addition

Protonation