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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6:49 minutes

Problem 20c,d

Textbook Question

What products are obtained from the reaction of the following compounds with one equivalent of Br₂, using FeBr₃ as a catalyst?
c.
d.

Verified step by step guidance

Analyze the structure of the compound provided. The molecule consists of two aromatic rings connected by an ester functional group (-COO-). Aromatic rings are susceptible to electrophilic substitution reactions, such as bromination.

Understand the role of FeBr3 as a catalyst. FeBr3 is a Lewis acid that reacts with Br2 to generate the electrophile, Br+, which is necessary for the bromination reaction.

Determine the directing effects of substituents on the aromatic rings. The ester group (-COO-) is an electron-withdrawing group, which deactivates the aromatic ring it is directly attached to and directs substitution to the meta position relative to itself. The other aromatic ring is unsubstituted and will undergo bromination more readily.

Predict the site of bromination. The unsubstituted aromatic ring is more reactive and will likely undergo bromination at one of its positions. The aromatic ring attached to the ester group is less reactive due to the electron-withdrawing effect, but if bromination occurs, it will be at the meta position relative to the ester group.

Conclude the reaction mechanism. The Br+ electrophile generated by FeBr3 will attack the most reactive site on the molecule, leading to the formation of brominated products. The exact positions of bromination depend on the reactivity of the rings and the directing effects of the substituents.

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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 process is facilitated by the resonance stabilization of the aromatic system, allowing the ring to maintain its aromaticity after substitution. In this case, bromine (Br2) acts as the electrophile, and the presence of a catalyst like FeBr3 enhances the reaction by generating a more reactive bromonium ion.

Role of Catalysts in EAS

Catalysts, such as FeBr3 in this reaction, are substances that increase the rate of a chemical reaction without being consumed in the process. In EAS, FeBr3 helps to generate a more electrophilic bromine species, facilitating the substitution reaction. The catalyst forms a complex with bromine, making it more reactive towards the aromatic compound, thus promoting the formation of the brominated product.

Regioselectivity in Substitution Reactions

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of EAS, the position where the electrophile substitutes on the aromatic ring can be influenced by the presence of substituents already on the ring. Electron-donating groups direct electrophiles to ortho and para positions, while electron-withdrawing groups direct them to the meta position, affecting the final product distribution.

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