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Which one of the following esters cannot undergo Claisen self-condensation?

1. CH3-CH2-CH2-CH2-COOCH2H5
2. C6H5COOC2H5
3. C6H5CH2COOC2H5
4. C6H11COOC2H5

Correct answer: C6H5COOC2H5

Solution

Claisen condensation requires the ester to have at least one α-hydrogen. Ethyl benzoate (C6H5COOC2H5) lacks α-hydrogens on the benzene ring, so it cannot undergo Claisen self-condensation.

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