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 52a

Textbook Question

Predict the product of the oxidation reactions shown.
(a)

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Identify the type of oxidation reaction. Common oxidizing agents in organic chemistry include KMnO4, CrO3, PCC, and others. Determine which oxidizing agent is used in the reaction.

Determine the functional group present in the starting material. Common functional groups that undergo oxidation include alcohols, aldehydes, and ketones.

Apply the rules of oxidation for the specific functional group. For example, primary alcohols typically oxidize to aldehydes and then to carboxylic acids, while secondary alcohols oxidize to ketones.

Consider any structural changes that might occur during the oxidation process. This includes changes in the carbon skeleton or the formation of new functional groups.

Draw the structure of the predicted product, ensuring that all changes from the oxidation process are accurately represented. Verify that the product is consistent with the expected outcome based on the oxidizing agent and the starting material.

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Key Concepts

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

Oxidation Reaction

Oxidation in organic chemistry involves the increase in the oxidation state of a molecule, typically by adding oxygen or removing hydrogen. This process often converts alcohols to aldehydes, ketones, or carboxylic acids, depending on the type of alcohol and the oxidizing agent used.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Understanding the functional group involved, such as alcohols, is crucial for predicting the outcome of oxidation reactions, as different groups react differently under oxidation conditions.

Oxidizing Agents

Oxidizing agents are substances that facilitate oxidation by accepting electrons from other molecules. Common oxidizing agents in organic chemistry include potassium permanganate (KMnO4), chromic acid (H2CrO4), and PCC (pyridinium chlorochromate). The choice of oxidizing agent can influence the final product of the reaction.

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Related Practice

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.

(n) sodium ethoxide + 2-methyl-2-bromobutane

(o) octan-1-ol + DMSO + oxalyl chloride

(p) 4-cyclopentylhexan-1-ol + DMP reagent

Textbook Question

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na₂Cr₂O₇/H₂SO₄, (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

a. octan-1-ol

b. octan-3-ol

Textbook Question

Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.

a. chromic acid

b. PCC (pyridinium chlorochromate)

c. sodium hypochlorite/acetic acid

Textbook Question

Predict the products formed by periodic acid cleavage of the following diols.

(a) CH₃CH(OH)CH(OH)CH₃

(b)

Textbook Question

Every oxidation is accompanied by a reduction. Identify the species that is reduced in the Swern oxidation in Assessment 13.48.

Textbook Question

Although trans-diols in rings cannot be cleaved using HIO₄ acyclic trans-diols can. Explain this discrepancy.

Textbook Question

Predict the product of the following oxidation reactions.

(b)

Textbook Question

δ-Hydroxyaldehydes are in equilibrium with their hemiacetal form. Predict the product that would form upon treatment of the hemiacetal with Dess–Martin periodinane.

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Predict the product of the oxidation reactions shown. (a)

Key Concepts

Oxidation Reaction

Functional Groups

Oxidizing Agents

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Predict the product of the oxidation reactions shown.
(a)