Formation and reactions of enols and enolates

Abstract

This chapter focuses on the formation and reactions of enols and enolates. Carbonyl compounds have two opposed sides to their characters. They can be nucleophilic as well: electrophilic attack on aldehydes, ketones, and acid derivatives is a useful reaction too. How can the same class of compound be subject to both nucleophilic and electrophilic attack? The resolution of this paradox is the subject of the chapter, showing that most carbonyl compounds exist in two forms: one electrophilic and one nucleophilic. The electrophilic form is the carbonyl compound itself and the nucleophilic form is called the enol. The chapter then considers tautomerism, enolization, and enol ethers.