MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition / Nucleophilic acyl substitution of carboxylic acid derivatives
JEE Advanced levelSingle correct optionDifficulty 3 of 3o1207

Acetic formic anhydride, , reacts with 1 equiv of methylamine at low temperature. The main product is

  1. Amethyl acetate
  2. BN-methylformamide
  3. Cmethyl formate
  4. DN-methylacetamide

Answer: B

The amine attacks the more electrophilic and less hindered formyl carbon (H instead of the electron-releasing, bulkier ). The acetate group is the leaving group, giving N-methylformamide and acetic acid.
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