NEET 2010 Chemistry question

Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is:

(1)
(2)
(3)
(4)Correct

Answer: (4)

Solution

Nucleophilic attack at the carbonyl carbon is easier when this carbon is more electron deficient and the leaving group is better. In the chlorine atom is strongly electron withdrawing (-I) and its lone pairs overlap poorly with the carbonyl (3p-2p mismatch), so there is very little resonance

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Question ID VK-090533