Ester Condensations
(Carey, Chap. 21)

Reaction Product Notes
 
Claisen condensation.
Must be able to form beta-
   ketoester enolate anion
   intermediate
 
Beta-ketoester cleavage;
reverse of ester condensation
 
Mixed ester condensation;
R'' must have no alpha H's
 
Mixed condensation-
ketone with ester;
beta-diketone product
 
Dieckmann cyclization.
Intramolecular ester
   condensation;
5 or 6 memb. rings only
 
Intramolecular ketone with
   ester condensation;
5 or 6 memb. rings only
 
Malonate ester alkylation
R' can be 1o or 2o
 
Decarboxylation of beta-
   carbonyl acid.
"Malonic ester synthesis"
Syn of substituted acids
 
Acetoacetic ester alkylation
R' can be 1o or 2o

 
Decarboxylation of beta-
   carbonyl acid.
"Acetoacetic ester synthesis"
Syn of substituted ketones
 
 
Michael reaction
 
Pre-formed ester enolate
R' must be 1o only
 
Pre-formed ester enolate
Mixed condensation with
   alde. or ketone

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