Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
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 Acids4h 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

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

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3:03 minutes

Problem 55

Textbook Question

Though ketones, like aldehydes, are in equilibrium with a hydrated form, they cannot be further oxidized. Why?

Verified step by step guidance

Understand the structure of ketones: Ketones have a carbonyl group (C=O) bonded to two carbon atoms. This makes them less reactive towards oxidation compared to aldehydes, which have a carbonyl group bonded to at least one hydrogen atom.

Examine the hydration equilibrium: The image shows a ketone in equilibrium with its hydrated form, a geminal diol. This equilibrium involves the addition of water across the carbonyl group, forming two hydroxyl groups on the same carbon.

Consider oxidation of ketones: For oxidation to occur, there must be a hydrogen atom on the carbonyl carbon that can be removed. In ketones, both groups attached to the carbonyl carbon are carbon groups, lacking the necessary hydrogen for further oxidation.

Compare with aldehydes: Aldehydes can be oxidized to carboxylic acids because they have a hydrogen atom on the carbonyl carbon, which can be replaced by an oxygen atom during oxidation.

Conclude why ketones cannot be further oxidized: Since ketones lack the hydrogen atom on the carbonyl carbon, they cannot undergo further oxidation to form carboxylic acids or other oxidized products.

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Key Concepts

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

Ketones and Aldehydes

Ketones and aldehydes are both carbonyl compounds characterized by a carbon atom double-bonded to an oxygen atom. Aldehydes have at least one hydrogen atom attached to the carbonyl carbon, while ketones have two carbon groups attached. This structural difference influences their reactivity and stability, particularly in oxidation reactions.

Hydration Equilibrium

Ketones and aldehydes can undergo hydration, forming their corresponding hydrate forms, which are typically more stable in aqueous solutions. This equilibrium between the carbonyl compound and its hydrate is crucial for understanding their behavior in solution, as it affects their reactivity and the extent to which they can participate in further chemical reactions.

Oxidation of Carbonyl Compounds

Oxidation refers to the process of increasing the oxidation state of a molecule, often involving the addition of oxygen or the removal of hydrogen. Ketones cannot be oxidized further because they already possess the highest oxidation state for a carbonyl group, while aldehydes can be oxidized to carboxylic acids. This limitation is due to the structural stability of ketones, which prevents further oxidation under typical conditions.

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