Question

Question: Draw a stepwise mechanism for the following reaction.

Short answer

Answer

Mechanism of hydrolysis of given lactam

Step-by-step solution

Step-by-Step Solution Step 1: Lactams

Organic compounds in which a carbonyl carbon is linked to the nitrogen of an amine group are called amides. It is formed by the condensation of carboxylic acids and mines.

When the acid amine condensation occurs within the same molecule, cyclic amides are formed and are called lactams.

Amide linkages are also called peptide bonds and are formed between amino acids during protein synthesis.

Hydrolysis of lactam

Lactams on hydrolysis give the bifunctional parent compound with an amino group and carboxylate group. These compounds are amino alkanoic acid.

The hydrolysis reaction is catalyzed either by an acid or a base.

Acid-catalyzed hydrolysis gives a product with a carboxyl group and quaternary ammonium group.

Base catalyzed hydrolysis gives an amino alkanoic acid with a carboxylate ion group and an amine group.

Hydrolysis of given lactam

The given reaction is a base-catalyzed hydrolysis reaction. The reaction is initiated by the attack of the hydroxide ion on the carbonyl carbon causing ring opening. The amide ion abstracts proton from the carboxylic acid group forming the final product.

Hydrolysis of the given lactam