Table of contents

1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

16. Carboxylic Acids and Their Derivatives

Amide Hydrolysis

GOB Chemistry

16. Carboxylic Acids and Their Derivatives

Amide Hydrolysis

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Problem 65a

Textbook Question

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.

Verified step by step guidance

Step 1: Understand the structure of epsilon-lactam. Epsilon-lactam is a six-membered cyclic amide, where the amide group is part of the ring. The structure includes a carbonyl group (C=O) bonded to a nitrogen atom within the ring.

Step 2: Recall the concept of acid hydrolysis of amides. Acid hydrolysis involves breaking the amide bond (C-N bond) in the presence of water and an acid catalyst, resulting in the formation of a carboxylic acid and an amine or ammonium ion.

Step 3: Identify the bond to be broken in epsilon-lactam. The hydrolysis reaction will cleave the bond between the carbonyl carbon and the nitrogen atom in the amide group.

Step 4: Predict the products of the reaction. Breaking the amide bond in epsilon-lactam will yield a carboxylic acid (with the carbonyl group) and an amine group (from the nitrogen atom). Since the reaction occurs in acidic conditions, the amine will likely be protonated to form an ammonium ion.

Step 5: Draw the structures of the products. The carboxylic acid product will have a straight-chain structure with a terminal carboxyl group (-COOH), and the ammonium ion will be represented as NH4+ (if fully protonated). Ensure the structures reflect the correct number of carbon atoms from the original epsilon-lactam ring.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Lactams

Lactams are cyclic amides formed when a carboxylic acid and an amine react within 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, including their reactivity in hydrolysis.

Acid Hydrolysis

Acid hydrolysis is a chemical reaction where a compound reacts with water in the presence of an acid, leading to the breakdown of the compound. In the case of lactams, acid hydrolysis results in the cleavage of the amide bond, yielding the corresponding carboxylic acid and amine. This process is essential for understanding how lactams can be transformed back into their constituent parts.

Amide Bond

An amide bond is a functional group formed between a carboxylic acid and an amine, characterized by a carbonyl group (C=O) adjacent to a nitrogen atom (N). This bond is pivotal in the structure of lactams and influences their stability and reactivity. Recognizing the nature of the amide bond is key to predicting the outcomes of reactions involving lactams, including hydrolysis.

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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.

Key Concepts

Lactams

Acid Hydrolysis

Amide Bond

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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.