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 51c

Textbook Question

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

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Identify the carbonyl compound in the image. The structure shown is a ketone, specifically a phenyl-2-propanone.

Recall that ketones are typically formed by the oxidation of secondary alcohols. Therefore, the alcohol precursor must be a secondary alcohol.

Examine the structure of the ketone. The carbonyl group is attached to a phenyl group and a propyl group, indicating that the secondary alcohol must have a hydroxyl group on the carbon that is bonded to both the phenyl and propyl groups.

Determine the structure of the alcohol. The secondary alcohol that would oxidize to form this ketone is 1-phenyl-2-propanol, where the hydroxyl group is on the second carbon of the propyl chain.

Understand the oxidation process. During oxidation, the hydroxyl group of the secondary alcohol is converted into a carbonyl group, resulting in the formation of the ketone shown in the image.

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Key Concepts

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

Alcohol Classification

Alcohols are classified into three categories: primary, secondary, and tertiary, based on the number of carbon atoms attached to the carbon bearing the hydroxyl (-OH) group. Primary alcohols can be oxidized to aldehydes, secondary alcohols to ketones, and tertiary alcohols generally do not oxidize to carbonyl compounds due to the lack of a hydrogen atom on the carbon bearing the -OH group.

Oxidation Reactions

Oxidation in organic chemistry refers to the process of increasing the oxidation state of a molecule, often involving the addition of oxygen or the removal of hydrogen. In the case of alcohols, oxidation typically converts them into carbonyl compounds, such as aldehydes or ketones, depending on the type of alcohol being oxidized.

Reagents for Oxidation

Common reagents used for the oxidation of alcohols include potassium dichromate (K2Cr2O7), chromium trioxide (CrO3), and pyridinium chlorochromate (PCC). The choice of reagent can influence the extent of oxidation, with some reagents selectively oxidizing primary alcohols to aldehydes while others may further oxidize them to carboxylic acids.

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Related Practice

Textbook Question

Predict the product of the oxidation reactions shown.

(b)

Textbook Question

If there is no water present, the hydrate of an aldehyde cannot form. Could an aldehyde itself (not the hydrate) be oxidized to a carboxylic acid? Why?

Textbook Question

In Hinkley, the cleanup continues today. In one process PG&E is using to mitigate the chromium(VI) toxicity, ethanol is injected into the soil. How would this reduce the chromium(VI) contamination?

Textbook Question

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

(b)

Textbook Question

Oxidation of the phenol shown gives a single quinone product. Predict this product and explain why it is the only one formed.

Textbook Question

Predict the product of the following oxidation reactions.

(c)

Textbook Question

Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.

(a)

Textbook Question

The intermediates for the Swern oxidation, a reaction introduced in Section 13.9.4, are shown. Provide the arrow-pushing mechanism that rationalizes the formation of each intermediate and the final product(s).

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

Key Concepts

Alcohol Classification

Oxidation Reactions

Reagents for Oxidation

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