Consider the nucleophilic substitution of ammonia to benzoyl chloride shown below. Which of the following statements is true?

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Question: Consider the nucleophilic substitution of ammonia to benzoyl chloride shown below. Which of the following statements is true?

Option a: Ammonia is the electrophile. In this reaction, ammonia acts as the nucleophile, attacking the carbonyl carbon of benzoyl chloride. The electrophilic center is the carbonyl carbon of benzoyl chloride, not the ammonia molecule. Therefore this statement is incorrect.

Option b: Benzoyl chloride is the nucleophile. This is the opposite of what happens: benzoyl chloride serves as the electrophile whose carbonyl carbon is attacked by the nucleophilic ammonia. Hence this option is also incorrect.

Option c: No reaction occurs because the amide product is less stable than benzoyl chloride. While stability considerations matter, acyl substitution by ammonia to form benzamide is a common and favorable process under appropriate conditions; the statement that no reaction occurs is not correct. The driving factors are nucleophilic attack and formation of a stable amide with chloride leaving group.

Option d: The benzoyl chloride is very reactive because the chloride anions are good leaving groups because they are stable in solution. This statement captures two key ideas: (1) chloride is a good leaving group in acyl substitution reactions, facilitating displacement by the nucleophile; (2) the resulting amide formation (benzamide) is thermodynamically accessible, aided by resonance stabilization of the acyl system and relief of strain. Thus this option correctly describes the reactivity trend observed for acyl chlorides reacting with nucleophiles like ammonia.

Option e: The benzoyl chloride is not very reactive because the chloride anions are poor leaving groups because they are not stable in solution. This is inaccurate: chloride is a reasonably stable leaving group in many solvent conditions, and acyl chlorides are indeed highly reactive toward nucleophiles. Therefore this statement is incorrect.

In summary, options a, b, c, and e misstate the roles or reactivity principles of the reagents, while option d correctly identifies that benzoyl chloride is highly reactive due to the good leaving ability of chloride in this acyl substitution context.

MCD4400 Chemistry II - Trimester 3 - 2025

Consider the nucleophilic substitution of ammonia to benzoyl chloride shown below. Which of the following statements is true?

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