Return to Contents  Chapter 21: Ester Enolates  Ch 21 contents
alkylation of an active methylene enolate
Reaction type : Nucleophilic substitution


double alkylation of an active methylene
double alkylation forming a cyclic system

Related Reactions

Step 1:
First, an acid-base reaction. The ethoxide functions as a base and removes an acidic a-hydrogen from between the two carbonyl groups 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 the alkylation product and a bromide ion.

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