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 Chapter 18: Enols and Enolates 
Ch 18 contents
Alkylation of Enolates
alkylation of an enolate
Reaction type : Nucleophilic substitution

Summary

Related Reactions
MECHANISM OF ALKYLATION OF ALDEHYDES AND KETONES
Step 1:
First, an acid-base reaction. Hydroxide functions as a base and removes the acidic α-hydrogen giving the reactive enolate.
mechanism of enolate alkylation
Step 2:
The nucleophilic enolate attacks the alkyl halide at the electrophilic carbon carrying the halogen via an SN2 type process giving alkylated ketone and a bromide ion.
 

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© Dr. Ian Hunt, Department of Chemistry, University of Calgary