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Question

Which one of the following would not give an appreciable yield of Claisen condensation product?

A
Ethyl hexanoate
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B
Ethyl 3-methyl hexanoate
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C
Ethyl 2-methyl hexanoate
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D
Ethyl 4-methyl hexanoate
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Solution

The correct option is C Ethyl 2-methyl hexanoate
The Claisen condensation is a carbon-carbon bond-forming reaction that occurs between two esters, or one ester and another carbonyl compound in the presence of a strong base, resulting in a -keto ester or a -diketone.

But in case of, ethyl 2-methyl hexanoate resulting product will not deprotonate to enolate which is essential for driving the reaction, so it will not perform this reaction.

Hence, the correct option is C.

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