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Which ester listed below cannot participate in Claisen self-condensation due to the absence of α-hydrogen atoms?

1. Ethyl benzoate (C6H5COOC2H5)
2. Ethyl acetate (CH3COOC2H5)
3. Ethyl propanoate (CH3CH2COOC2H5)
4. Ethyl butanoate (CH3CH2CH2COOC2H5)

Correct answer: Ethyl benzoate (C6H5COOC2H5)

Solution

Claisen condensation requires the presence of an α-hydrogen atom in the ester. C6H5COOC2H5 (ethyl benzoate) lacks an α-hydrogen atom because the carbonyl group is directly attached to a benzene ring, which does not have hydrogens on the α-carbon.

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