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Question

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 Cl atoms, Cl 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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