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

Electron Withdrawing Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Electron Withdrawing Groups

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5:36 minutes

Problem 18e

Textbook Question

Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.
(e) Reagents: toluene + HNO₃, H₂SO₄, heat
Desired Product: 2,4,6-trinitrotoluene (TNT)

Verified step by step guidance

Step 1: Analyze the reaction conditions. The image shows a nitrobenzene reacting with tert-butyl chloride in the presence of a catalyst, likely aluminum chloride (AlCl₃). This suggests a Friedel-Crafts alkylation reaction.

Step 2: Understand the mechanism of Friedel-Crafts alkylation. The tert-butyl chloride reacts with AlCl₃ to form a highly reactive tert-butyl carbocation, which serves as the electrophile in the reaction.

Step 3: Predict the regioselectivity of the reaction. The nitro group (-NO₂) on the benzene ring is an electron-withdrawing group, which deactivates the ring and directs electrophilic substitution to the meta position relative to itself.

Step 4: Determine the major product. The tert-butyl carbocation will attack the meta position of the nitrobenzene, resulting in the formation of the product shown in the image: 1-nitro-3-tert-butylbenzene.

Step 5: Verify the reaction feasibility. Friedel-Crafts alkylation is generally not efficient on strongly deactivated rings like nitrobenzene. However, under specific conditions, the reaction may proceed to give the desired product in moderate yield.

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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. In the context of the question, toluene undergoes EAS when treated with a mixture of nitric acid and sulfuric acid, generating nitronium ions (NO2+) that act as the electrophile. The position of substitution is influenced by the electron-donating properties of the methyl group in toluene.

Regioselectivity in Aromatic Reactions

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. In the case of toluene nitration, the methyl group directs the incoming nitro group to the ortho and para positions due to its electron-donating effect, leading to the formation of 2,4,6-trinitrotoluene (TNT) as the desired product. Understanding regioselectivity is crucial for predicting the major products of aromatic substitution reactions.

Catalysis and Reaction Conditions

Catalysis involves the use of a substance to increase the rate of a chemical reaction without being consumed in the process. In this scenario, aluminum chloride acts as a catalyst, enhancing the electrophilic substitution reaction. The reaction conditions, including temperature and the presence of strong acids, are vital for achieving a good yield of the desired product, as they influence the reactivity of the electrophile and the stability of intermediates formed during the reaction.

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