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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Problem 34j

Textbook Question

Predict the product(s) of the following reactions.
(j)

Verified step by step guidance

Identify the functional groups present in the starting material. The compound is a ketone with an aromatic ring and an alkyl group attached.

Recognize the reagents used in the reaction: KMnO4, KOH, H2O, and heat. This combination is typically used for oxidative cleavage of alkenes or oxidation of alkyl side chains on aromatic rings.

Understand that KMnO4 under basic conditions (KOH) and heat will oxidize the alkyl side chain on the aromatic ring to a carboxylic acid.

Predict that the methyl group attached to the aromatic ring will be oxidized to a carboxylic acid group, resulting in the formation of a benzoic acid derivative.

Consider the stability of the aromatic ring during the reaction. The aromatic ring itself remains intact, while the side chain is oxidized to form the carboxylic acid product.

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Key Concepts

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

Side-Chain Oxidation

Side-chain oxidation involves the conversion of alkyl side chains on aromatic rings into carboxylic acids. This reaction typically uses strong oxidizing agents like potassium permanganate (KMnO4) under basic conditions. The process is selective for benzylic positions, where the carbon atom is directly attached to the aromatic ring, leading to the formation of carboxylic acids.

Role of Potassium Permanganate (KMnO4)

Potassium permanganate (KMnO4) is a powerful oxidizing agent used in organic chemistry to oxidize various functional groups. In the context of side-chain oxidation, KMnO4 oxidizes alkyl groups attached to aromatic rings, particularly at benzylic positions, converting them into carboxylic acids. The reaction typically requires basic conditions and heat to proceed efficiently.

Benzylic Oxidation

Benzylic oxidation refers to the oxidation of a benzylic carbon, which is the carbon atom adjacent to an aromatic ring. This position is particularly reactive due to the stability provided by the aromatic ring. In the presence of oxidizing agents like KMnO4, benzylic carbons are preferentially oxidized to form carboxylic acids, making this a key step in transforming alkylbenzenes into benzoic acids.

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Predict the product(s) of the following reactions.(j)

Key Concepts

Side-Chain Oxidation

Role of Potassium Permanganate (KMnO4)

Benzylic Oxidation

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Predict the product(s) of the following reactions.
(j)