Which of the following shows the weakest electrophilic character of carbonyl carbon?

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Solution

Electrophilic character of carbonyl carbons depends on electronegativity of attached atoms and also resonance electron donating capability o atoms. Because of highest electronegativity (among $4$ molecules) of $C l$ atoms, $C l$ atom withdraws from carbonyl carbon and as a result it has highest electrophilic character.
But among $A, C$ and $D$ all have resonance but in $D$ (thioester) resonance is not good as in $A$ and $C$ due orbitals mismatched this resonance is most powerful in $C$ . As a result electrophilic character of $C$ will be lowed.

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