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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5:02 minutes

Problem 47

Textbook Question

Propose a synthetic sequence of this trisubstituted benzene starting from toluene.

Verified step by step guidance

Step 1: Begin with toluene as the starting material. Toluene is a methyl-substituted benzene, which can undergo electrophilic substitution reactions due to the activating effect of the methyl group.

Step 2: Perform nitration of toluene using a mixture of concentrated HNO₃ and H₂SO₄. This introduces a nitro group (-NO₂) at the ortho and para positions relative to the methyl group. The para product is typically favored due to steric hindrance.

Step 3: Brominate the nitrotoluene product using Br₂ in the presence of FeBr₃ as a catalyst. Bromination occurs at the remaining ortho position relative to the methyl group, as the nitro group is meta-directing and the methyl group is ortho/para-directing.

Step 4: Oxidize the methyl group to a carboxylic acid (-COOH) using a strong oxidizing agent such as KMnO₄ or Na₂Cr₂O₇ under acidic conditions. This converts the methyl group into a benzoic acid functional group.

Step 5: If necessary, adjust the halogen substituent (e.g., convert Br to Cl) using a halogen exchange reaction such as Finkelstein reaction or Sandmeyer reaction, depending on the desired halogen substituent in the final product.

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Key Concepts

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

Electrophilic Aromatic Substitution (EAS)

Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This reaction is crucial for synthesizing substituted aromatic compounds, as it allows for the introduction of various functional groups onto the benzene ring. Understanding the mechanism of EAS, including the role of activating and deactivating groups, is essential for proposing synthetic routes.

Directing Effects of Substituents

Substituents on an aromatic ring influence the position where new substituents can be added through EAS. Activating groups, such as -OH or -NH2, direct incoming electrophiles to the ortho and para positions, while deactivating groups, like -NO2 or -Cl, typically direct to the meta position. Recognizing these directing effects is vital for planning the synthetic sequence to achieve the desired trisubstituted benzene compound.

Functional Group Transformations

Functional group transformations involve converting one functional group into another through various chemical reactions. In the context of synthesizing the target compound from toluene, transformations such as oxidation, halogenation, and nitration may be employed. Mastery of these transformations is necessary to navigate the synthetic pathway effectively and achieve the desired final product.

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Show how you would synthesize the following aromatic derivatives from benzene.

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Starting from toluene, propose a synthesis of this trisubstituted benzene.

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