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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3:46 minutes

Problem 18

Textbook Question

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

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Identify the substituents on each benzene ring.

Determine the electronic effects of each substituent: whether they are electron-donating or electron-withdrawing.

Recall that electron-donating groups (EDGs) activate the benzene ring towards electrophilic aromatic substitution, while electron-withdrawing groups (EWGs) deactivate it.

Compare the substituents: the benzene with the strongest electron-withdrawing group will be the least reactive.

Select the benzene with the most deactivating substituent as the least reactive in electrophilic aromatic substitution.

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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 reaction is crucial for synthesizing various aromatic compounds. 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 a benzene ring can be classified as activating or deactivating based on their electronic effects. Activating groups, such as -OH or -NH2, donate electron density to the ring, increasing its reactivity towards electrophiles. In contrast, deactivating groups, like -NO2 or -CF3, withdraw electron density, making the ring less reactive in EAS reactions. Understanding these effects is essential for predicting the reactivity of substituted benzenes.

Ortho/Para vs. Meta Directing

The position of substituents on a benzene ring affects the orientation of subsequent electrophilic substitutions. Activating groups are typically ortho/para directing, meaning they favor substitution at the ortho or para positions relative to themselves. Deactivating groups, however, are usually meta directing, leading to substitution at the meta position. This distinction is important for determining the least reactive substituted benzene in EAS reactions.

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Related Practice

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:

e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzene

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, 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?

Textbook Question

A mixture of 0.10 mol benzene and 0.10 mol p-xylene was allowed to react with 0.10 mol nitronium ion until all the nitronium ion was gone. Two products were obtained: 0.002 mol of one and 0.098 mol of the other.

b. Why was more of one product obtained than of the other?

Textbook Question

Indigo is a dye that was originally isolated from coal tar. In 1905, Johann Friedrich Wilhelm Adolf von Baeyer won a Nobel Prize for a method that allowed indigo to be isolated from plants [a green chemist ahead of his time.] If you nitrated indigo using the reaction learned in this chapter, at which carbon would you expect the nitro group to attach?

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