Question

The most susceptible to nucleophilic attack at the carbonyl group among the given compounds is

• A. CH\(_3\)COOCH\(_3\)
• B. CH\(_3\)CONH\(_2\)
• C. CH\(_3\)COOCH\(_3\) (repeated option, likely meant CH\(_3\)COOH)
• D. CH\(_3\)COCl

Hint:

The reactivity of carboxylic acid derivatives is governed by the basicity of the leaving group. A weaker base is a better leaving group.

Answer 1

The Correct Option is D

Step 1: Understanding the Concept:
Nucleophilic attack on a carbonyl group is favored by a more electron-deficient carbonyl carbon. This is enhanced by electron-withdrawing groups attached to the carbonyl.

Step 2: Detailed Explanation:
The reactivity order of carboxylic acid derivatives towards nucleophilic substitution is: \[ \text{Acyl chloride} > \text{Anhydride} > \text{Ester} > \text{Amide} \] This is because the leaving group ability follows: Cl\(^-\) > RCOO\(^-\) > RO\(^-\) > NH\(_2^-\). Cl is the best leaving group and also a strong electron-withdrawing group, making the carbonyl carbon highly electrophilic. Therefore, among the given, CH\(_3\)COCl is most susceptible to nucleophilic attack.

Step 3: Final Answer:
CH\(_3\)COCl is the most susceptible, which corresponds to option (D).