Chapter 21.6, Problem 7LTS

Interpretation Introduction

Interpretation:

The conversion of trimethylacetone converted to 6, 6-dimethyl-5-oxoheptanal should be explained.

Concept introduction:

The addition of an enamine to $\alpha ,\beta$-unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis.  The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized.  The product is then hydrolyzed by an aqueous acid to produce 1, 5-dicarbonyl compound.  Steps involved in Stork enamine synthesis are,

• Formation of an enamine
• Michael addition
• Hydrolysis