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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5:34 minutes

Problem 55e

Textbook Question

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzene

Verified step by step guidance

Step 1: Understand the concept of electrophilic aromatic substitution (EAS). EAS reactions involve the substitution of a hydrogen atom on an aromatic ring with an electrophile. The reactivity of the aromatic ring depends on the electronic effects of substituents already present on the ring, which can either activate or deactivate the ring toward electrophilic attack.

Step 2: Analyze the substituents on each compound. Substituents can be electron-donating groups (EDGs) or electron-withdrawing groups (EWGs). EDGs increase the electron density on the aromatic ring, making it more reactive toward electrophiles, while EWGs decrease the electron density, making the ring less reactive. For the given compounds: - p-Methylnitrobenzene has a methyl group (EDG) and a nitro group (EWG). - 2-Chloro-1-methyl-4-nitrobenzene has a chloro group (weak EWG), a methyl group (EDG), and a nitro group (strong EWG). - 1-Methyl-2,4-dinitrobenzene has a methyl group (EDG) and two nitro groups (strong EWGs). - p-Chloromethylbenzene has a methyl group (EDG) and a chloro group (weak EWG).

Step 3: Evaluate the net electronic effects of the substituents on the aromatic ring. Consider the relative strength of the activating and deactivating groups. For example, nitro groups are strong deactivators due to their strong electron-withdrawing nature, while methyl groups are weak activators. The presence of multiple nitro groups will significantly reduce the reactivity of the ring.

Step 4: Rank the compounds based on their reactivity toward EAS. The compound with the most electron-donating substituents and the least electron-withdrawing substituents will be the most reactive. Conversely, the compound with the most electron-withdrawing substituents will be the least reactive. Consider the positions of the substituents as well, as ortho/para-directing groups can influence the reactivity differently than meta-directing groups.

Step 5: Finalize the ranking. Based on the analysis, rank the compounds from most reactive to least reactive toward electrophilic aromatic substitution. Use the electronic effects of the substituents and their positions on the aromatic ring to determine the order.

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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. The reactivity of the aromatic compound is influenced by the nature of substituents already present on the ring, which can either activate or deactivate the ring towards further substitution.

Activating and Deactivating Groups

Substituents on an aromatic ring can be classified as activating or deactivating based on their electronic effects. Activating groups, such as alkyl groups, increase the electron density of the ring, making it more reactive towards electrophiles. In contrast, deactivating groups, like nitro groups, withdraw electron density, reducing reactivity and directing electrophilic attacks to specific positions on the ring.

Ortho/Para vs. Meta Directing Effects

The position of substituents on an aromatic ring affects the site of electrophilic attack. Activating groups typically direct new substituents to the ortho and para positions, while deactivating groups often direct them to the meta position. Understanding these directing effects is crucial for predicting the reactivity and product distribution in electrophilic aromatic substitution reactions.

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Related Practice

Textbook Question

For each horizontal row of substituted benzenes, indicate

a. the one that is the most reactive in an electrophilic aromatic substitution reaction.

Textbook Question

List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:

b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzene

Textbook Question

List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:

a. benzene, phenol, toluene, nitrobenzene, bromobenzene

Textbook Question

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

b. 1-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, 1-methyl-2,4-dinitrobenzene

Textbook Question

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene

Textbook Question

For each horizontal row of substituted benzenes, indicateb. the one that is the least reactive in an electrophilic aromatic substitution reaction.

Textbook Question

For each horizontal row of substituted benzenes, indicate

c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.

Textbook Question

Why is anisole nitrated more rapidly than thioanisole under the same conditions?

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Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzene

Key Concepts

Electrophilic Aromatic Substitution (EAS)

Activating and Deactivating Groups

Ortho/Para vs. Meta Directing Effects

Watch next

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzene