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Question

The given compound is obtained by Claisen condensation of ?

A
Ethyl-2-methyl pentanoate
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B
Ethyl-5-methyl hexanoate
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C
Ethyl-4-methyl pentanoate
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D
Ethyl-3,3-dimethyl butanoate
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Solution

The correct option is C Ethyl-4-methyl pentanoate
Ester undergoes self condensation in presence of strong base to give β-ketoester. This reaction is called Claisen condensation reaction.

Mechanism of Claisen condensation reaction:
1. Enolate formation : The strong base will abstract the acidic α-hydrogen to form the enolate ion.

2. Nucleophile attack: Formed enolate will attack the carbonyl carbon of another ester molecule and leaving group (-OR) will leave the compound to form β ketoester.

The given product is a self condensation product and from the product we can predict that the leaving group is OEt and the enolate ion formed at α- position of ester.
Hence, the possible reactant of the claisen condensation reaction is Ethyl-4-methyl penatanoate.


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