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

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BlackTom AI · Accepted Answer

The question asks about the nucleophilic addition to benzoyl chloride with ammonia and which statement is true.
Option a: 'No reaction occurs because the amide product is less stable than benzoyl chloride.' This is not accurate. Amide formation from acyl chlorides by amines is a common, favorable reaction driven by formation of a stable amide and by the good leaving group chloride, so claiming no reaction occurs is incorrect.
Option b: 'Chloride anions are poor leaving groups because they are not stable in solution.' In general, chloride is a decent leaving group in acyl substitutions because it can be stabilized by solvation in many solvents; this statement is too absolute and contradicts typical acyl substitution chemistry, making it incorrect.
Option c: 'Chloride anions are good leaving groups because they are stable in solution.' This aligns with standard organic chemistry: chloride is stabilized by solvation in polar solvents, and in acyl transfer reactions the chloride leaves as Cl−, facilitating nucleophilic acyl substitution to form an amide. The stability of the leaving group in solution is a key factor that makes this process favorable, so this statement is true.
Option d: 'Ammonia is the electrophile.' In this reaction, ammonia acts as the nucleophile attacking the electrophilic carbonyl carbon of benzoyl chloride; therefore, ammonia is not the electrophile, making this option incorrect.
Option e: 'Benzoyl chloride is the nucleophile.' Benzoyl chloride is the electrophile in this mechanism (the acyl chloride carbonyl carbon is attacked by ammonia); thus describing benzoyl chloride as the nucleophile is incorrect.
Overall, identifying the true statement requires recognizing that the leaving group ability of chloride in acyl substitutions is tied to its solvation and stability as Cl−, which supports option c as the correct choice. The remaining options misstate roles (electrophile vs nucleophile) or rely on inaccurate generalizations about reactivity, leading to their invalidity.

CHM1052 - MUM S2 2025 Week 6: Preparation quiz

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

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