When both the carboxylic acid and the amine are in the same molecule, amide formation produces lactams. A lactam is a cyclic amide, where the amide group is part of the ring. Draw the structure of the product(s) obtained from acid hydrolysis of these lactams.


a. <IMAGE> epsilon-lactam

Verified step by step guidance

1. Identify the structure of the epsilon-lactam, which is a cyclic amide with a five-carbon chain between the nitrogen and the carbonyl group, forming a six-membered ring.
2. Understand that acid hydrolysis of an amide involves breaking the amide bond, which is the bond between the carbonyl carbon and the nitrogen atom.
3. Recognize that during hydrolysis, the amide bond is cleaved, resulting in the formation of a carboxylic acid and an amine. In the case of a lactam, this will open the ring structure.
4. Draw the open-chain structure that results from the hydrolysis, showing the carboxylic acid group (COOH) and the amine group (NH2) at the ends of the chain.
5. Ensure that the carbon chain length and connectivity remain consistent with the original lactam structure, resulting in a linear molecule with the functional groups at the ends.

Key Concepts

Lactams

Lactams are cyclic amides formed when a carboxylic acid and an amine are part of the same molecule, resulting in a ring structure that includes the amide group. They are classified based on the size of the ring, with epsilon-lactams being six-membered rings. Understanding lactams is crucial for predicting their chemical behavior, especially during hydrolysis.

Acid Hydrolysis

Acid hydrolysis is a chemical reaction where water and an acid are used to break down compounds, such as lactams, into their constituent parts. In the case of lactams, this process typically results in the formation of the corresponding carboxylic acid and amine. Recognizing the conditions and products of acid hydrolysis is essential for understanding the transformation of lactams.

Amide Group

The amide group is a functional group characterized by a carbonyl (C=O) bonded to a nitrogen atom (N). It plays a significant role in the structure and reactivity of lactams. The properties of the amide group influence the stability and reactivity of lactams during hydrolysis, making it a key concept in organic chemistry.