Propose a mechanism for the hydrolysis of N,N-dimethylacetamide (b) under acidic conditions.

Verified step by step guidance

1. Protonate the carbonyl oxygen of N,N-dimethylacetamide using an acid, increasing the electrophilicity of the carbonyl carbon.
2. Nucleophilic attack by water on the carbonyl carbon occurs, forming a tetrahedral intermediate.
3. Proton transfer within the tetrahedral intermediate leads to the formation of a good leaving group.
4. The leaving group, N,N-dimethylamine, departs, resulting in the formation of a protonated carboxylic acid.
5. Deprotonation of the protonated carboxylic acid by water or another base in the solution yields the final carboxylic acid product.

Key Concepts

Hydrolysis Mechanism

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of amides, hydrolysis typically involves the conversion of the amide into a carboxylic acid and an amine or ammonia. Understanding the mechanism requires knowledge of nucleophilic attack, protonation, and the role of water as a reactant.

Acidic Conditions

Acidic conditions refer to an environment where the pH is less than 7, often achieved by adding a strong acid. In hydrolysis reactions, acids can protonate the carbonyl oxygen of the amide, increasing its electrophilicity and making it more susceptible to nucleophilic attack by water. This step is crucial for facilitating the hydrolysis process.

Nucleophilic Attack

Nucleophilic attack is a fundamental concept in organic chemistry where a nucleophile, a species with a high electron density, attacks an electrophile, a species with a low electron density. In the hydrolysis of N,N-dimethylacetamide, water acts as the nucleophile that attacks the carbonyl carbon of the amide, leading to the formation of a tetrahedral intermediate, which is essential for the reaction to proceed.