MolSynapsequestion bank
MolSynapse / Question bank / Reduction, Oxidation and Hydrolysis in Organic Chemistry / Jones vs PCC and hydrolysis of drawn esters, amides, nitriles
JEE Main levelSingle correct optionDifficulty 2 of 3ro270

The compound shown is boiled with aqueous HCl. What are the main products?

  1. ABenzylamine and methanoic acid
  2. BBenzoic acid and methylammonium chloride
  3. CBenzaldehyde and methylamine
  4. DBenzoic acid and methanol

Answer: B

The compound is N-methylbenzamide. Acidic hydrolysis of an amide cleaves the C-N bond: the acyl part becomes benzoic acid and the nitrogen part leaves as the protonated amine, methylammonium chloride (the amine is trapped as its salt by the acid, which drives the reaction). The other options have the wrong cleavage or involve a carbon-carbon bond.
Practice Reduction, Oxidation and Hydrolysis in Organic Chemistry More on Jones vs PCC and hydrolysis of drawn esters, amides, nitriles

More questions on Jones vs PCC and hydrolysis of drawn esters, amides, nitriles