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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Problem 40c

Textbook Question

Predict the major product of the following electrophilic aromatic substitution reactions.
(c)

Verified step by step guidance

Identify the functional groups present in the molecule. The molecule contains an amide group attached to a benzene ring. The amide group is a moderate deactivating group and directs electrophilic substitution to the meta position.

Recognize the reagents used in the reaction. Bromine (Br₂) in the presence of aluminum bromide (AlBr₃) is a typical setup for bromination, an electrophilic aromatic substitution reaction.

Understand the role of AlBr₃. Aluminum bromide acts as a Lewis acid, facilitating the formation of the bromonium ion (Br⁺), which is the active electrophile in the reaction.

Determine the directing effects of the amide group. The amide group is a meta-directing group due to its electron-withdrawing nature, which means the bromine will likely add to the meta position relative to the amide group on the benzene ring.

Predict the major product. Given the conditions and the directing effects, the major product will be the bromination of the benzene ring at the meta position relative to the amide group. Since 2 equivalents of Br₂ are used, two bromine atoms will be added to the meta positions.

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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 reaction where an electrophile replaces a hydrogen atom on an aromatic ring. The aromatic ring acts as a nucleophile, and the reaction typically involves a catalyst to generate a more reactive electrophile. In this context, the benzene ring in the amide is the site of substitution, and the reaction conditions favor bromination.

Directing Effects of Substituents

Substituents on an aromatic ring influence the position where new groups are added during EAS. Electron-donating groups (EDGs) direct new substituents to ortho and para positions, while electron-withdrawing groups (EWGs) direct them to the meta position. The amide group in the given compound is an electron-withdrawing group, which typically directs electrophiles to the meta position.

Role of Lewis Acid Catalysts

Lewis acids, such as AlBr3, are used in EAS to enhance the electrophilicity of halogens like Br2. The Lewis acid forms a complex with the halogen, making it a more potent electrophile that can effectively attack the aromatic ring. This is crucial in facilitating the bromination of the benzene ring in the presence of the amide group.

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