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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4:20 minutes

Problem 43a

Textbook Question

Predict the major product at the end of each sequence.
(a)

Verified step by step guidance

Step 1: Analyze the first reaction in the sequence. The benzene ring undergoes sulfonation when treated with SO₃ and H₂SO₄. This reaction introduces a sulfonic acid group (-SO₃H) onto the benzene ring. The sulfonation typically occurs at one of the positions on the aromatic ring.

Step 2: Consider the second reaction in the sequence. The benzene ring with the sulfonic acid group reacts with Cl₂ in the presence of AlCl₃, which is a Friedel-Crafts halogenation reaction. This reaction introduces a chlorine atom onto the benzene ring.

Step 3: Determine the regioselectivity of the reactions. The sulfonic acid group (-SO₃H) is a meta-directing group due to its electron-withdrawing nature. Therefore, the chlorine atom will be added to the meta position relative to the sulfonic acid group.

Step 4: Draw the intermediate product after the sulfonation step, showing the benzene ring with the -SO₃H group attached. Then, draw the final product after the halogenation step, showing the benzene ring with both the -SO₃H group and the chlorine atom in the meta position.

Step 5: Verify the major product by considering the stability and reactivity of the intermediates formed during the sequence. Ensure that the substitution pattern aligns with the directing effects of the functional groups involved.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is facilitated by the stability of the aromatic system, which allows the ring to undergo temporary disruption to accommodate the electrophile. Common electrophiles include halogens, nitronium ions, and sulfonium ions, making EAS a key mechanism for functionalizing aromatic compounds.

Sulfonation

Sulfonation is a specific type of electrophilic aromatic substitution where a sulfonyl group (–SO3H) is introduced into an aromatic ring. This reaction typically uses sulfur trioxide (SO3) in the presence of concentrated sulfuric acid (H2SO4) as a catalyst. The resulting sulfonic acid group is a strong electron-withdrawing group, which can influence the reactivity of the aromatic compound in subsequent reactions.

Chlorination of Aromatics

Chlorination of aromatics involves the introduction of chlorine atoms into an aromatic ring, typically using chlorine gas (Cl2) in the presence of a Lewis acid catalyst like aluminum chloride (AlCl3). This reaction also follows the electrophilic aromatic substitution mechanism, where the chlorine acts as the electrophile. The presence of the Lewis acid enhances the electrophilicity of chlorine, facilitating the substitution process and leading to the formation of chlorinated aromatic products.

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Predict the major product at the end of each sequence.(a)

Key Concepts

Electrophilic Aromatic Substitution

Sulfonation

Chlorination of Aromatics

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Predict the major product at the end of each sequence.
(a)