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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Problem 51a

Textbook Question

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(a)

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Examine the given carbonyl compound structure. The image shows a ketone with a carbonyl group (C=O) attached to a secondary carbon atom.

Identify the position of the carbonyl group in the structure. In this case, the carbonyl group is on the second carbon of a four-carbon chain, indicating a ketone.

Recall that secondary alcohols are oxidized to form ketones. Therefore, the alcohol precursor must have had a hydroxyl group (-OH) on the same carbon that now holds the carbonyl group.

Determine the structure of the alcohol. Replace the carbonyl group (C=O) with a hydroxyl group (-OH) on the same carbon to revert the ketone back to its corresponding alcohol.

The resulting alcohol structure is 2-butanol, which is a secondary alcohol. This alcohol, when oxidized, would produce the given ketone structure.

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Key Concepts

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

Alcohol Oxidation

Alcohols can be oxidized to form carbonyl compounds, such as aldehydes and ketones. The oxidation process involves the removal of hydrogen atoms or the addition of oxygen, which transforms the hydroxyl (-OH) group of the alcohol into a carbonyl (C=O) group. The type of alcohol (primary, secondary, or tertiary) determines the product formed during oxidation.

Types of Alcohols

There are three main types of alcohols: primary, secondary, and tertiary. Primary alcohols can be oxidized to aldehydes, while secondary alcohols can be oxidized to ketones. Tertiary alcohols, however, do not undergo oxidation to form carbonyl compounds due to the lack of a hydrogen atom on the carbon bearing the hydroxyl group.

Oxidizing Agents

Oxidizing agents are substances that facilitate the oxidation of alcohols by accepting electrons. Common oxidizing agents include potassium dichromate (K2Cr2O7), chromium trioxide (CrO3), and sodium hypochlorite (NaOCl). The choice of oxidizing agent can influence the reaction conditions and the specific carbonyl compound produced from the alcohol.

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Related Practice

Textbook Question

Predict the product of the following reactions.

(b)

Textbook Question

Draw a mechanism for the following oxidation reactions.

(b)

Textbook Question

Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.

(b)

Textbook Question

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

Textbook Question

Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.

(a)

Textbook Question

Unfortunately, the use of NMO creates an additional green chemistry problem. What is the problem and how might it be solved?

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O. If no reaction occurs, write 'no reaction.'

(a)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (xi) HOCl, H₂O (xii) HIO₄. If no reaction occurs, write 'no reaction.'

(a)

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Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.(a)

Key Concepts

Alcohol Oxidation

Types of Alcohols

Oxidizing Agents

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Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(a)