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 57d

Textbook Question

Give the structures of compounds C through D in the following series of reactions.

Verified step by step guidance

Step 1: Analyze the first reaction. The benzene ring reacts with an acyl chloride (CH3CH2COCl) in the presence of AlCl3, a Lewis acid catalyst. This is a Friedel-Crafts acylation reaction, which introduces an acyl group (CH3CH2CO-) onto the benzene ring, forming compound A.

Step 2: Examine the second reaction. Compound A undergoes nitration using HNO3 and H2SO4. This introduces a nitro group (-NO2) onto the benzene ring, typically at the meta position relative to the acyl group due to the electron-withdrawing nature of the acyl group, forming compound B.

Step 3: Consider the third reaction. Compound B is treated with Zn(Hg) and HCl, which is a Clemmensen reduction. This reduces the acyl group (CH3CH2CO-) to an alkyl group (CH3CH2-), forming compound C.

Step 4: Analyze the final reaction. Compound C is oxidized using hot, concentrated KMnO4. This strong oxidizing agent converts the alkyl group (CH3CH2-) attached to the benzene ring into a carboxylic acid group (-COOH), forming compound D.

Step 5: Summarize the transformations. Compound A is formed via Friedel-Crafts acylation, compound B via nitration, compound C via Clemmensen reduction, and compound D via oxidation with KMnO4. Each step involves a specific functional group transformation on the benzene ring.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this reaction, the aromatic compound acts as a nucleophile, attacking the electrophile, which leads to the formation of a new bond. The presence of a catalyst, such as AlCl3, is often required to generate a more reactive electrophile, facilitating the substitution process.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In the context of organic chemistry, this often refers to the conversion of carbonyl compounds to alcohols or alkenes. The reaction shown with Zn(Hg) and HCl indicates a reduction process, where a carbonyl group is reduced to an alkane, typically through a Clemmensen reduction, which is useful for transforming ketones or aldehydes into hydrocarbons.

Oxidation Reactions

Oxidation reactions in organic chemistry involve the loss of electrons or an increase in oxidation state, often resulting in the conversion of alcohols to carbonyl compounds or carboxylic acids. The use of KMnO4 in hot, concentrated conditions indicates a strong oxidizing environment, which can oxidize alcohols to carboxylic acids or aldehydes to carboxylic acids, depending on the starting material. This step is crucial for understanding the transformation from compound C to D in the reaction sequence.

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