In this chapter we look at the chemistry of enolates of esters and active methylene systems.
Recall that we have previously looked at the enolates of aldehydes and ketones.
What we will see here is analogous to that material and can be treated in a very similar fashion.
Before continuing, you should make sure you are familiar with the reactions where the esters are attacked by nucleophiles due to the electrophilic character of the carbonyl C and undergo nucleophilic substitution (Chapter 20)
 

Treatment of esters with a suitable base can lead to the formation of a nucleophilic species called an enolate that will react with an electrophile. These C nucleophiles are useful for making new carbon-carbon bonds.

Enolates

• Ester enolates
• Common bases used for preparing enolates
• Active methylenes
• pKa of various a-hydrogen systems

• Overview of ester enolate reactions
• Claisen condensation
• Dieckmann condensation

• Acylation of Ketone enolates with esters
• Reactions of Active methylenes:
• Alkylation
• Decarboxylation
• Michael additions
• Acetoacetic ester synthesis
• Malonic ester synthesis

• Sample problem

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