Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids3h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

25. Condensation Chemistry

Condensation Reactions

Organic Chemistry

25. Condensation Chemistry

Condensation Reactions

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3:31 minutes

Problem 22Bruice - 8th Edition

Textbook Question

Co2 + catalyzes the hydrolysis of the lactam shown here. Propose a mechanism for the metal-ion catalyzed reaction.

Verified step by step guidance

Identify the functional groups in the lactam structure, focusing on the amide bond that will undergo hydrolysis.

Recognize that Co^{2+} can act as a Lewis acid, coordinating with the carbonyl oxygen of the lactam to increase the electrophilicity of the carbonyl carbon.

Propose that a water molecule, activated by the Co^{2+} ion, attacks the electrophilic carbonyl carbon, leading to the formation of a tetrahedral intermediate.

Consider the breakdown of the tetrahedral intermediate, where the nitrogen atom is protonated and the C-N bond is cleaved, resulting in the formation of a carboxylic acid and an amine.

Conclude the mechanism by showing the regeneration of the Co^{2+} ion, which can catalyze further hydrolysis reactions.

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Key Concepts

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

Lactam Hydrolysis

Lactams are cyclic amides that can undergo hydrolysis, a reaction where water breaks the amide bond, leading to the formation of a carboxylic acid and an amine. Understanding the structure of lactams and the conditions under which hydrolysis occurs is crucial for proposing a mechanism. The reaction typically involves nucleophilic attack by water, facilitated by a catalyst.

Metal-Ion Catalysis

Metal-ion catalysis involves the use of metal ions to enhance the rate of a chemical reaction. In the context of lactam hydrolysis, metal ions can stabilize the transition state or activate the substrate, making it more susceptible to nucleophilic attack. Common metal ions used in catalysis include zinc, copper, and magnesium, which can coordinate with the lactam and facilitate the reaction.

Mechanistic Pathways

A mechanistic pathway outlines the step-by-step sequence of events that occur during a chemical reaction. For the metal-ion catalyzed hydrolysis of a lactam, it is essential to identify the key intermediates and transition states involved. This includes the initial coordination of the metal ion to the lactam, the nucleophilic attack by water, and the eventual breakdown of the lactam ring, leading to product formation.