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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5:58 minutes

Problem 54a

Textbook Question

Predict the major products of bromination of the following compounds, using Br₂ and FeBr₃ in the dark.
(a)

Verified step by step guidance

Step 1: Analyze the structure of the compound provided. The molecule consists of two benzene rings connected by a single bond. One ring has a nitro group (-NO2) attached, and the other ring has a methoxy group (-OCH3) attached.

Step 2: Understand the directing effects of the substituents. The nitro group is an electron-withdrawing group and acts as a meta-director, while the methoxy group is an electron-donating group and acts as an ortho/para-director.

Step 3: Predict the reactivity of each benzene ring. The ring with the nitro group will be less reactive toward electrophilic bromination due to the electron-withdrawing nature of the nitro group. The ring with the methoxy group will be more reactive due to the electron-donating nature of the methoxy group.

Step 4: Determine the positions where bromination is likely to occur. Bromination will preferentially occur on the benzene ring with the methoxy group at the ortho and para positions relative to the methoxy group, as these positions are activated by the electron-donating effect.

Step 5: Use the catalyst FeBr3 to facilitate the bromination reaction. FeBr3 helps generate the electrophilic bromine species (Br+) from Br2, which then reacts with the activated positions on the benzene ring with the methoxy group.

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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 this process, the aromatic system retains its stability while introducing new substituents. The reaction typically involves the generation of a sigma complex, followed by deprotonation to restore aromaticity.

Activating and Deactivating Groups

Substituents on an aromatic ring can either activate or deactivate the ring towards electrophilic substitution. Activating groups, such as -OCH3, increase the electron density of the ring, making it more reactive, while deactivating groups, like -NO2, withdraw electron density and make the ring less reactive. The nature of these groups also influences the position where substitution occurs.

Regioselectivity in Bromination

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. In the bromination of aromatic compounds, the presence of activating or deactivating groups affects where the bromine will add on the ring. For example, activating groups direct substitution to the ortho and para positions, while deactivating groups typically direct it to the meta position.

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Related Practice

Textbook Question

What are the products of the following reactions?

Textbook Question

Rank the following compounds from most reactive to least reactive in an electrophilic aromatic substitution reaction:

Textbook Question

For each of the statements in Column I, choose a substituent from Column II that fits the description for the compound on the right:

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Textbook Question

Predict the site(s) of electrophilic attack on these compounds.

Textbook Question

Predict the major products of bromination of the following compounds, using Br₂ and FeBr₃ in the dark.

(b)

Textbook Question

Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark.

(c)

Textbook Question

Predict the major products formed when benzene reacts (just once) with the following reagents.

f. fuming sulfuric acid

Textbook Question

Biphenyl is two benzene rings joined by a single bond. The site of substitution for a biphenyl is determined by (1) which phenyl ring is more activated (or less deactivated), and (2) which position on that ring is most reactive, using the fact that a phenyl substituent is activating and ortho, para-directing.

a. Use resonance forms of a sigma complex to show why a phenyl substituent should be ortho, para-directing.

(i)

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Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark. (a)

Key Concepts

Electrophilic Aromatic Substitution (EAS)

Activating and Deactivating Groups

Regioselectivity in Bromination

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Predict the major products of bromination of the following compounds, using Br₂ and FeBr₃ in the dark.
(a)