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 59d

Textbook Question

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

Verified step by step guidance

Identify the functional group present in the starting material. In this case, the compound is a secondary alcohol, as indicated by the OH group attached to a carbon atom that is connected to two other carbon atoms.

Recognize the reagent used for the oxidation. Pyridinium chlorochromate (PCC) is a mild oxidizing agent that is commonly used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones without further oxidation to carboxylic acids.

Determine the type of oxidation reaction. Since the starting material is a secondary alcohol, PCC will oxidize it to a ketone.

Predict the structure of the product. The secondary alcohol will be converted to a ketone by replacing the OH group with a carbonyl group (C=O) at the same carbon atom.

Draw the structure of the product. The cyclohexane ring remains unchanged, and the carbon atom that was bonded to the OH group now forms a double bond with an oxygen atom, resulting in a ketone.

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Key Concepts

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

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule, atom, or ion. In organic chemistry, these reactions often involve the addition of oxygen or the removal of hydrogen. Understanding the specific type of oxidation, such as whether it is a mild or strong oxidation, is crucial for predicting the products formed.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying the functional groups present in the reactants is essential for predicting the products of oxidation reactions, as different groups react differently under oxidative conditions.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of how a chemical reaction occurs, detailing the bond-breaking and bond-forming processes. Understanding the mechanism of oxidation reactions helps in predicting the products, as it provides insight into the intermediates formed and the final structure of the product based on the starting materials.

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Related Practice

Textbook Question

Predict the products formed when cyclohexanone reacts with the following reagents.

g. Tollens reagent

Textbook Question

Oxidation of a phenol derivative produces the lactone shown. Provide an arrow-pushing mechanism that rationalizes this outcome.

Textbook Question

Identify the aromatic product that would result from the oxidation of the triol with an excess of PCC.

Textbook Question

A chemist attempted to oxidize a primary alcohol to a carboxylic acid using chromic acid. The product shown was obtained as a major component in the mixture. Suggest an arrow-pushing mechanism that accounts for its formation. [Think about what chromic acid would normally do to a phenol and make a list of bonds formed and bonds broken.]

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?

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