Chapter 18: Enols and Enolates

In this chapter we look at another type of reactivity of carbonyl compounds where they function as nucleophiles.
Before starting this, you should make sure you are familiar with the contrasting reactions where the aldehydes and ketones are attacked by nucleophiles due to the electrophilic character of the carbonyl C and undergo nucleophilic addition (Chapter 17)

Treatment of aldehydes and ketones with a suitable base can lead to the formation of a nucleophilic species called an enolate that reacts with electrophiles. These C nucleophiles are useful for making new carbon-carbon bonds.

Enols and Enolates

• Enols, Enolates, Tautomerism
• Acidity of the α-hydrogens

• Overview of enolate reactions
• Halogenation: acidic, or basic
• Haloform reaction
• Alkylation
• The aldol reaction: aldehydes, ketones, advanced aspects
• Conjugated systems
• Conjugate addition reactions
• Conjugate addition with Organocopper reagents
• The Michael Reaction
• The Robinson Annulation Reaction

• Sample Problems

© Dr. Ian Hunt, Department of Chemistry