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 53

Textbook Question

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

Verified step by step guidance

Identify the functional groups present in the starting material. The compound is a triol, meaning it has three hydroxyl (OH) groups attached to a cyclohexane ring.

Understand the role of PCC (Pyridinium Chlorochromate) in oxidation reactions. PCC is a mild oxidizing agent that can oxidize primary alcohols to aldehydes and secondary alcohols to ketones without further oxidation to carboxylic acids.

Consider the structure of the triol. The hydroxyl groups are attached to a cyclohexane ring, which can be oxidized to form carbonyl groups (either aldehydes or ketones).

Recognize that the presence of excess PCC suggests that all oxidizable alcohol groups will be converted to carbonyl groups. In this case, the triol will be oxidized to a compound with three carbonyl groups.

Determine the final structure. The oxidation of the triol with excess PCC will result in the formation of a compound with three ketone groups, which can undergo further rearrangement to form an aromatic compound, such as a quinone, due to the stabilization provided by the aromaticity.

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Key Concepts

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

Oxidation with PCC

Pyridinium chlorochromate (PCC) is a reagent used to oxidize alcohols to carbonyl compounds. In excess, PCC can further oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. Understanding the role of PCC in transforming hydroxyl groups is crucial for predicting the final aromatic product in this reaction.

Aromaticity

Aromatic compounds are characterized by their cyclic, planar structure with conjugated pi electrons following Huckel's rule (4n+2 pi electrons). The transformation of the triol into an aromatic product involves the formation of a stable, conjugated ring system. Recognizing the conditions that lead to aromaticity is essential for identifying the final product.

Triol Structure

A triol is a molecule containing three hydroxyl groups. In the given structure, these groups are attached to a cyclohexane ring. The oxidation process will convert these hydroxyl groups into carbonyl groups, facilitating the formation of an aromatic compound. Understanding the initial structure helps in predicting the changes during the reaction.

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Related Practice

Textbook Question

Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions.)

(a) CH₃CH₂CH₂COCH₃

(b) CH₃CH₂CH₂CH₂CHO

Textbook Question

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

b. Tollens reagent

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

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 oxidation reactions.

(d)

Textbook Question

Predict the product of the following reactions.

(b)

Textbook Question

Draw a mechanism for the following oxidation reactions.

(b)

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