MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition / Nucleophilic acyl substitution of carboxylic acid derivatives
JEE Main levelSingle correct optionDifficulty 2 of 3o1178

Acetyl chloride hydrolyses much faster than benzoyl chloride under the same conditions mainly because

  1. Abenzoyl chloride cannot form a tetrahedral intermediate
  2. Bin benzoyl chloride the phenyl ring conjugates with , reducing the electrophilicity of the carbonyl carbon
  3. Cthe methyl group is a strong electron-withdrawing group
  4. D is a poorer leaving group in benzoyl chloride

Answer: B

Resonance between the benzene ring and the carbonyl group delocalises charge and lowers the partial positive charge on the carbonyl carbon of benzoyl chloride. Methyl is electron-releasing, not withdrawing; the leaving group (Cl) is identical, and both form tetrahedral intermediates.
Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Nucleophilic acyl substitution of carboxylic acid derivatives

More questions on Nucleophilic acyl substitution of carboxylic acid derivatives