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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1:25 minutes

Problem 51b

Textbook Question

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

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Examine the structure of the given carbonyl compound. It is a ketone, characterized by a carbonyl group (C=O) bonded to two carbon atoms.

Identify the carbon atoms adjacent to the carbonyl group. In this structure, the carbonyl group is bonded to a cyclopentane ring and a tertiary butyl group.

Determine the alcohol precursor for the ketone. Ketones are typically formed from secondary alcohols through oxidation.

Consider the structure of the secondary alcohol that would lead to this ketone. The secondary alcohol would have a hydroxyl group (-OH) attached to the carbon that is bonded to the cyclopentane ring and the tertiary butyl group.

Visualize the transformation: The secondary alcohol undergoes oxidation, where the hydroxyl group is converted into a carbonyl group, resulting in 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 Oxidation

Alcohol oxidation involves the conversion of alcohols into carbonyl compounds, such as aldehydes or ketones, through the removal of hydrogen atoms. Primary alcohols typically oxidize to aldehydes, while secondary alcohols convert to ketones. The process can be facilitated by oxidizing agents like potassium dichromate or PCC (pyridinium chlorochromate). Understanding the type of alcohol and the conditions of oxidation is crucial for predicting the resulting carbonyl compound.

Types of Alcohols

Alcohols are classified into three categories: primary, secondary, and tertiary. Primary alcohols have the hydroxyl group (-OH) attached to a carbon that is connected to only one other carbon, secondary alcohols are attached to a carbon connected to two others, and tertiary alcohols are connected to three. This classification affects their reactivity and the products formed during oxidation, making it essential to identify the type of alcohol when predicting the outcome of oxidation reactions.

Carbonyl Compounds

Carbonyl compounds are organic molecules that contain a carbon atom double-bonded to an oxygen atom (C=O). They include aldehydes and ketones, which differ in the position of the carbonyl group. Aldehydes have the carbonyl group at the end of the carbon chain, while ketones have it within the chain. Recognizing the structure and properties of these compounds is vital for understanding the products of alcohol oxidation and their potential applications in organic synthesis.

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Related Practice

Textbook Question

(a) Based on Figure 24.23, explain why meta-dihydroxybenzene is not oxidized to meta-quinone.

(b) If a meta-quinone is not produced, what would you expect the product of the oxidation of meta-dihydroxybenzene to be?

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.

(c)

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)

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

Key Concepts

Alcohol Oxidation

Types of Alcohols

Carbonyl Compounds

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