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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1:33 minutes

Problem 2d

Textbook Question

Predict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
d. cyclohexanone

Verified step by step guidance

Step 1: Understand the nature of the reagents. Chromic acid (H₂CrO₄) and excess sodium hypochlorite (NaOCl) with acetic acid are strong oxidizing agents. PCC (pyridinium chlorochromate) and NaOCl with TEMPO are mild oxidizing agents. These reagents are used to oxidize alcohols or other functional groups depending on the substrate.

Step 2: Analyze the substrate, cyclohexanone. Cyclohexanone is a ketone, which is already in its most oxidized form for a simple carbonyl compound. Strong oxidizing agents like chromic acid or excess NaOCl will not further oxidize a ketone under typical conditions.

Step 3: Consider the reaction with PCC or NaOCl (1 equivalent) with TEMPO. These mild oxidizing agents are typically used to oxidize primary alcohols to aldehydes or secondary alcohols to ketones. Since cyclohexanone is already a ketone, no reaction is expected under these conditions.

Step 4: Summarize the expected outcomes. For both sets of reagents (strong and mild oxidizing agents), cyclohexanone is unlikely to undergo further oxidation because it is already a ketone, which is resistant to oxidation under normal conditions.

Step 5: Conclude that cyclohexanone remains unchanged when treated with the given reagents. This is an important concept in organic chemistry: ketones are generally stable to oxidation unless very harsh conditions are applied, which are not specified in this problem.

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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 of a molecule. In organic chemistry, common oxidizing agents like chromic acid and sodium hypochlorite facilitate the conversion of alcohols to carbonyl compounds or further oxidize aldehydes to carboxylic acids. Understanding the nature of these reactions is crucial for predicting the products formed when specific compounds are treated with these reagents.

PCC and TEMPO as Oxidizing Agents

Pyridinium chlorochromate (PCC) and TEMPO (2,2,6,6-tetramethylpiperidinyl-1-oxyl) are selective oxidizing agents used in organic synthesis. PCC is often employed to oxidize primary alcohols to aldehydes without over-oxidation to carboxylic acids, while TEMPO is used for mild oxidation reactions, particularly in the presence of NaOCl. Recognizing their specific reactivity helps in predicting the outcomes of reactions involving these agents.

Functional Group Transformations

Functional group transformations refer to the chemical reactions that convert one functional group into another, altering the properties and reactivity of the compound. In the context of cyclohexanone, understanding how ketones react under different oxidation conditions is essential for predicting the final products. This concept is fundamental in organic synthesis, where the goal is often to modify compounds to achieve desired functionalities.