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Nucleophilic Addition at the Carbonyl

Question

Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is:
$C H_{3} C O O C H_{3}$
$C H_{3} C O N H_{2}$
$C H_{3} C O O C O C H_{3}$
$C H_{3} C O C l$

A

C H_{3} C O C l

B

C H_{3} C O N H_{2}

C

C H_{3} C O O C H_{3}

D

C H_{3} C O O C O C H_{3}

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Solution

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This concept is related to nucleophilic addition reaction.

In acetyl chloride [ $C H_{3} C O C l$ ], due to the presence of Cl group and its negative inductive effect, carbonyl carbon is more deficient. Also, because of the larger size of Cl, resonance interaction does not occur between Cl and carbonyl carbon. So, the electronegativity of $C l$ plays a role, making nucleophilic addition occur more easily.

Order of nucleophillic addition = acyl chloride > acid anhydride > carboxylic acid > ester > amide

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