MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition / Carbonyl reactivity and acyl substitution
JEE Advanced levelSingle correct optionDifficulty 3 of 3o1259

The acid chloride shown is first treated with two equivalents of methylamine, and the isolated product is then reduced with excess lithium aluminium hydride followed by work-up. Which structure is the final product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

Ethanoyl chloride reacts with methylamine to give N-methylethanamide (the second equivalent of amine neutralises HCl). Lithium aluminium hydride reduces the amide C=O to CH2, giving N-methylethanamine, a secondary amine with an N-ethyl group. The alcohol would be the product only if the C-N bond were cleaved, which does not occur with amides.
Practice Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition More on Carbonyl reactivity and acyl substitution

More questions on Carbonyl reactivity and acyl substitution