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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5:18 minutes

Problem 49

Textbook Question

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

Verified step by step guidance

Step 1: Begin with toluene (C6H5CH3) as the starting material. The methyl group on toluene is an activating group that directs electrophilic substitution reactions to the ortho and para positions.

Step 2: Perform a bromination reaction using Br2 and FeBr3 as a catalyst. This will introduce a bromine atom at the ortho position relative to the methyl group due to the activating effect of the methyl group.

Step 3: Oxidize the methyl group to a carboxylic acid group (-COOH) using a strong oxidizing agent such as KMnO4 or Na2Cr2O7 under acidic conditions. This converts toluene into benzoic acid with a bromine substituent at the ortho position.

Step 4: Introduce the amino group (-NH2) at the para position relative to the carboxylic acid group. This can be achieved by performing a nitration reaction using HNO3 and H2SO4 to add a nitro group (-NO2) at the para position, followed by reduction of the nitro group to an amino group using a reducing agent like Sn/HCl or Fe/HCl.

Step 5: If necessary, adjust the halogen substituent (e.g., convert Br to Cl) using a halogen exchange reaction such as Finkelstein reaction or other halogen substitution methods to achieve the desired final product structure.

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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, such as the trisubstituted benzene in the question. Understanding the mechanism of EAS, including the role of activating and deactivating groups, is essential for predicting the outcomes of reactions starting from toluene.

Directing Effects of Substituents

Substituents on an aromatic ring influence the position where new substituents will be added during electrophilic aromatic substitution. Activating groups, like -NH2, direct incoming electrophiles to the ortho and para positions, while deactivating groups, like -Cl, direct them to the meta position. Recognizing these directing effects is vital for planning the synthesis of the desired trisubstituted benzene from toluene.

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, transformations such as nitration, reduction, and halogenation may be employed. Understanding these transformations allows chemists to strategically modify the starting material, toluene, into the desired product with specific functional groups like -COOH and -Cl.

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