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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2:38 minutes

Problem 70a

Textbook Question

What are the products of the following reactions?
a.

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Analyze the given reactant structure: The molecule contains a benzene ring attached to a side chain with a tertiary carbon and two methyl groups.

Identify the reagent: H₂CrO₄ (chromic acid) is a strong oxidizing agent, typically used to oxidize primary and secondary alcohols, as well as benzylic carbons.

Determine the reaction site: The benzylic position (the carbon directly attached to the benzene ring) is susceptible to oxidation by chromic acid, especially if it has hydrogen atoms attached.

Predict the product: Chromic acid will oxidize the benzylic carbon to a carboxylic acid group, replacing the entire side chain beyond the benzylic carbon with a -COOH group.

Conclude the reaction: The final product will be benzoic acid, as the benzylic carbon is oxidized to a carboxylic acid group, and the rest of the side chain is removed.

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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

Aromatic compounds can undergo oxidation reactions, where the addition of oxygen or the removal of hydrogen occurs. In this case, the presence of H2CrO4, a strong oxidizing agent, facilitates the oxidation of the side chain of the aromatic compound, typically converting alkyl groups into carbonyl groups or carboxylic acids, depending on the structure and conditions.

Chromic Acid (H2CrO4) as an Oxidizing Agent

Chromic acid (H2CrO4) is a powerful oxidizing agent commonly used in organic chemistry to oxidize alcohols, aldehydes, and side chains of aromatic compounds. It can convert primary alcohols to carboxylic acids and secondary alcohols to ketones, making it essential for understanding the products of oxidation reactions involving aromatic compounds.

Mechanism of Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. Understanding EAS is crucial for predicting the outcomes of reactions involving aromatic compounds, especially when considering how substituents on the ring can influence the reactivity and orientation of further reactions.

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