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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2:09 minutes

Problem 59b

Textbook Question

Predict the product of the following oxidation reactions.
(b)

Verified step by step guidance

Identify the functional group present in the starting material. Oxidation reactions typically involve alcohols, aldehydes, or ketones. Determine which functional group is present in the compound you are working with.

Select the appropriate oxidizing agent for the reaction. Common oxidizing agents include potassium permanganate (KMnO₄), chromium trioxide (CrO₃), and pyridinium chlorochromate (PCC). The choice of oxidizing agent can affect the outcome of the reaction.

Consider the conditions under which the oxidation is taking place. For example, acidic or basic conditions can influence the reaction pathway and the final product.

Predict the transformation based on the functional group and oxidizing agent. For instance, primary alcohols typically oxidize to aldehydes and then to carboxylic acids, while secondary alcohols oxidize to ketones.

Draw the structure of the expected product, ensuring that you account for any changes in the oxidation state of the carbon atoms involved in the reaction. Use structural formulas to clearly represent the changes.

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Key Concepts

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

Oxidation Reaction

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

Types of Alcohols

Alcohols are classified as primary, secondary, or tertiary based on the number of carbon atoms attached to the carbon bearing the hydroxyl group. Primary alcohols can be oxidized to aldehydes and further to carboxylic acids, secondary alcohols to ketones, while tertiary alcohols generally resist oxidation due to the lack of hydrogen atoms on the carbon.

Common Oxidizing Agents

Common oxidizing agents in organic chemistry include potassium permanganate (KMnO4), chromium trioxide (CrO3), and pyridinium chlorochromate (PCC). Each agent has specific conditions and selectivity, influencing the outcome of the oxidation reaction, such as PCC being used for mild oxidation to convert primary alcohols to aldehydes without further oxidation to carboxylic acids.

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Textbook Question

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

(a) CH₃CH(OH)CH(OH)CH₃

(b)

Textbook Question

Predict the product of the oxidation reactions shown.

(a)

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

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

Textbook Question

Tertiary (3°)alcohols are not oxidized by chromic acid. Why?

Textbook Question

Fill in the missing reactant, reagent, or product for each of the following oxidation reactions. react similarly to chromic acid

(d)

Textbook Question

Predict the product of the following reactions.

(a)

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