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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Multiple Choice

Rank the following in order of increasing rate of electrophilic aromatic bromination (slowest to fastest).

II < IV < I < III

I < II < IV < III

IV < III < II < I

III < II < I < IV

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Verified step by step guidance

Identify the substituents on each benzene ring: Compound I has a nitro group (NO2), Compound II has an aldehyde group (CHO), Compound III has a dimethylamino group (N(CH3)2), and Compound IV has a tert-butyl group (C(CH3)3).

Understand the effect of each substituent on the benzene ring: The nitro group is a strong electron-withdrawing group, the aldehyde group is a moderate electron-withdrawing group, the dimethylamino group is a strong electron-donating group, and the tert-butyl group is a weak electron-donating group.

Recall that electron-donating groups activate the benzene ring towards electrophilic aromatic substitution, while electron-withdrawing groups deactivate the ring.

Rank the compounds based on the activation or deactivation of the benzene ring: The compound with the strongest electron-donating group (III) will have the fastest rate of bromination, followed by the compound with the weaker electron-donating group (IV). The compound with the moderate electron-withdrawing group (II) will be slower, and the compound with the strong electron-withdrawing group (I) will be the slowest.

Based on the analysis, the order of increasing rate of electrophilic aromatic bromination is: I < II < IV < III.