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 57c

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the first reaction. The starting material is benzene, and it reacts with isobutyryl chloride (CH3CH(CH3)COCl) in the presence of AlCl3. This is a Friedel-Crafts acylation reaction, where the acyl group (CH3CH(CH3)CO-) is introduced onto the benzene ring to form compound A.

Step 2: Understand the mechanism of Friedel-Crafts acylation. AlCl3 acts as a Lewis acid, facilitating the generation of the acylium ion (CH3CH(CH3)C+=O), which is the electrophile. This electrophile reacts with benzene to form the ketone product (compound A).

Step 3: Examine the second reaction. Compound A undergoes a Clemmensen reduction using Zn(Hg) and HCl. This reaction reduces the carbonyl group (C=O) in compound A to a methylene group (-CH2-), resulting in compound C.

Step 4: Understand the Clemmensen reduction mechanism. Zn(Hg) in acidic conditions reduces the ketone functional group to an alkane, effectively removing the oxygen atom and replacing it with two hydrogen atoms.

Step 5: Summarize the transformations. Compound A is formed by the acylation of benzene with isobutyryl chloride, introducing a ketone group. Compound C is formed by reducing the ketone group in compound A to a methylene group via Clemmensen reduction.

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as it describes the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the types of bonds formed or broken during the reaction. Familiarity with mechanisms helps predict the outcome of reactions and the structures of the resulting compounds.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is essential for predicting the behavior of organic compounds during reactions. Each functional group has distinct properties and reactivity patterns, which influence the overall structure of the compounds involved.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is important for understanding isomerism, where compounds with the same molecular formula can have different structures and properties. Knowledge of stereochemistry is vital when determining the correct structures of products in a series of reactions, especially when chiral centers are involved.

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