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

EAS:Retrosynthesis

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Retrosynthesis

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Problem 84

Textbook Question

Acetohexamide is used to treat type 2 diabetes that cannot be well controlled by diet alone. Fill in the blanks of the synthetic scheme used to synthesize acetohexamide. [Hints have been provided below each step.]

Verified step by step guidance

Step 1: Begin with the chlorination of benzene using Cl₂ and FeCl₃ as a catalyst. This will introduce a chlorine atom onto the benzene ring, forming chlorobenzene.

Step 2: Perform a Friedel-Crafts acylation on chlorobenzene using CH₃COCl and AlCl₃. This will add an acetyl group to the benzene ring, resulting in the formation of 4-chloroacetophenone.

Step 3: Treat 4-chloroacetophenone with NaNH₂. This step involves the conversion of the acetyl group to an amine group, forming 4-chloroaniline.

Step 4: React 4-chloroaniline with HCl and NaNO₂ to form a diazonium salt. This is a key intermediate for further transformations.

Step 5: Convert the diazonium salt to a sulfonyl chloride using AcOH, SO₂, and Cu₂Cl₂. This will yield 4-chlorobenzenesulfonyl chloride, which can then react with cyclohexyl isocyanate to form acetohexamide.

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Key Concepts

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

Friedel-Crafts Acylation

Friedel-Crafts acylation is a reaction that introduces an acyl group into an aromatic ring using an acyl chloride and a Lewis acid catalyst, such as AlCl3. This reaction is crucial for forming aromatic ketones, as seen in the initial step of the synthetic scheme for acetohexamide, where benzene is acylated to form an acylated aromatic compound.

Diazotization and Sandmeyer Reaction

Diazotization involves converting an aromatic amine into a diazonium salt using nitrous acid (HNO2), typically generated in situ from NaNO2 and HCl. The Sandmeyer reaction then allows the transformation of the diazonium group into various functional groups, such as halides or nitriles, using copper(I) salts. This is a key step in modifying aromatic compounds, as seen in the synthetic pathway for acetohexamide.

Sulfonyl Chloride Formation and Reaction

Sulfonyl chlorides are formed by reacting aromatic compounds with chlorosulfonic acid or SO2Cl2, often in the presence of a catalyst. These compounds are reactive intermediates that can undergo further reactions, such as nucleophilic substitution, to form sulfonamides. In the synthesis of acetohexamide, the formation and subsequent reaction of a sulfonyl chloride intermediate is a critical step in constructing the final product.

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