Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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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2:38 minutes

Problem 18b

Textbook Question

What are the products of the following reactions? a.
b.

Verified step by step guidance

Identify the functional groups in the starting material. Here, we have an aromatic ring (benzene) with an alkyl side chain.

Recognize the reagent used in the reaction. H2CrO4 (chromic acid) is a strong oxidizing agent.

Understand the type of reaction. Chromic acid will oxidize the benzylic position (the carbon directly attached to the benzene ring) to a carboxylic acid.

Determine the changes to the side chain. The entire alkyl side chain will be oxidized to a carboxylic acid group (-COOH) at the benzylic position.

Draw the final product, which will be benzoic acid (benzene ring with a carboxylic acid group attached).

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Key Concepts

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

Oxidation of Aromatic Compounds

Oxidation of aromatic compounds involves the introduction of oxygen or the removal of hydrogen, often leading to the formation of carbonyl groups or carboxylic acids. In the presence of strong oxidizing agents like H2CrO4, side-chain oxidation can occur, converting alkyl groups attached to the aromatic ring into more oxidized functional groups, such as ketones or carboxylic acids.

Chromic Acid (H2CrO4) as an Oxidizing Agent

Chromic acid (H2CrO4) is a powerful oxidizing agent commonly used in organic chemistry to oxidize alcohols and alkenes, as well as to oxidize alkyl side chains on aromatic compounds. It facilitates the conversion of primary and secondary alcohols to aldehydes and ketones, respectively, and can further oxidize these to carboxylic acids, depending on the reaction conditions.

Reaction Conditions and Mechanism

The reaction conditions, such as temperature and the presence of catalysts, significantly influence the outcome of oxidation reactions. In this case, heating (indicated by Δ) with H2CrO4 promotes the oxidation of the alkyl side chain of the aromatic compound, leading to the formation of specific products. Understanding the mechanism of these reactions helps predict the products formed during the oxidation process.