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

19. Reactions of Aromatics: EAS and Beyond

Side-Chain Oxidation

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Side-Chain Oxidation

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2:10 minutes

Problem 35a

Textbook Question

Suggest the reagents used to effect the transformations shown.
(a)

Verified step by step guidance

Identify the starting material and the product. The starting material is a hydroquinone with an aldehyde group, and the product is a benzoquinone with a carboxylic acid group.

Recognize the transformation involved: the conversion of the aldehyde group to a carboxylic acid group, and the oxidation of the hydroquinone to benzoquinone.

Consider the reagents typically used for oxidizing hydroquinones to benzoquinones. Common oxidizing agents include potassium dichromate (K2Cr2O7) or silver oxide (Ag2O).

For the conversion of an aldehyde to a carboxylic acid, a mild oxidizing agent such as Tollens' reagent (Ag(NH3)2+) or Jones reagent (CrO3, H2SO4) can be used.

Combine the knowledge of both transformations to suggest a reagent or a sequence of reagents that can achieve both the oxidation of the hydroquinone and the aldehyde to carboxylic acid. A strong oxidizing agent like potassium permanganate (KMnO4) in acidic conditions can be effective for both transformations.

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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 increase in oxidation state of a molecule, often by the addition of oxygen or the removal of hydrogen. In organic chemistry, oxidizing agents such as chromic acid or potassium permanganate are commonly used to convert alcohols or aldehydes to carboxylic acids or ketones. Understanding the role of oxidizing agents is crucial for predicting the outcome of such transformations.

Quinone Formation

Quinones are a class of cyclic organic compounds characterized by a fully conjugated cyclic dione structure. They are typically formed through the oxidation of phenols. In the given transformation, the conversion of a hydroquinone to a quinone involves the oxidation of the phenolic hydroxyl groups to carbonyl groups, which is a key step in the synthesis of quinones.

Reagent Selection for Oxidation

Selecting the appropriate reagent for oxidation is critical in organic synthesis. Common reagents include PCC, PDC, and Jones reagent, each with specific applications and selectivity. For the transformation of hydroquinone to benzoquinone, reagents like silver oxide or ferric chloride are often used due to their ability to selectively oxidize phenolic groups without over-oxidizing the molecule.

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