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Fill in the blanks. The base to form the enolate of the ester in a Claisen condensation must match the __________ side of the ester because of NaOH is used, _______________ occurs instead of enolate formation.

Fill in the blanks. The base to form the enolate of the ester in a Claisen condensation must match the __________ side of the ester because of NaOH is used, _______________ occurs instead of enolate formation.


I think the first answer is alcohol? I'm not sure about that and what the answer is for the 2nd blank.


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Answer #1

The base used to form the enolate of the ester in a claisen condensation must match the alcohol side of the ester because if NaOH is used, saponification reaction occur instead of enolate formation.

The base used in claisen condensation should match the alcohol side of the ester. Generally, the alkoxide ion of the alcohol part of the ester is used as a base. It's to avoid the trans-esterification reaction. If we used a strong base like sodium hydroxide then the hydrolysis of ester takes place resulting in the formation of salts of carboxylic acid (saponification reaction).


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