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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Problem 45c

Textbook Question

Predict the major product of the following electrophilic aromatic substitution reactions.
(c)

Verified step by step guidance

Identify the type of reaction: The reaction shown is an electrophilic aromatic substitution (EAS), where a nitro group (NO2) will be introduced to the aromatic ring.

Determine the directing effects of substituents: The benzene ring has a chlorine (Cl) substituent, which is an ortho/para-directing group due to its electron-withdrawing nature through resonance, and a carbonyl group (C=O) which is a meta-directing group due to its electron-withdrawing nature through induction.

Consider the reaction conditions: The presence of HNO3 and H2SO4 indicates a nitration reaction, where the nitronium ion (NO2+) is the electrophile.

Predict the major product: Given the presence of both ortho/para and meta-directing groups, the position of the nitro group will be influenced by the stronger directing effect. The chlorine group, being ortho/para-directing, will favor substitution at the ortho or para position relative to itself.

Select the most likely position: The para position relative to the chlorine is less sterically hindered compared to the ortho position, making it the most favorable site for nitration. Therefore, the major product will have the nitro group at the para position relative to the chlorine substituent.

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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 reaction where an aromatic ring, such as benzene, undergoes substitution of a hydrogen atom by an electrophile. This process involves the formation of a highly reactive intermediate called an arenium ion, which is stabilized by resonance. The reaction typically requires a strong acid to generate the electrophile, as seen with the use of HNO3 and H2SO4 to produce the nitronium ion (NO2+).

Directing Effects of Substituents

Substituents on an aromatic ring influence the position where new groups are added during EAS. Electron-donating groups (EDGs) generally direct new substituents to the ortho and para positions, while electron-withdrawing groups (EWGs) direct them to the meta position. In the given structure, the chlorine atom is an ortho/para director due to its lone pairs, while the carbonyl group is a meta director due to its electron-withdrawing nature.

Reactivity and Orientation in EAS

The reactivity and orientation in EAS are influenced by the nature of substituents on the aromatic ring. In the given molecule, the presence of both a chlorine atom and a carbonyl group creates competing directing effects. Chlorine, being a weak electron-donating group, directs ortho/para, while the carbonyl group, a strong electron-withdrawing group, directs meta. The major product is often determined by the stronger directing influence, which in this case is the meta-directing carbonyl group.

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Related Practice

Open Question

Draw the resonance contributors for:

a. benzaldehyde

Textbook Question

Despite the amino group being an ortho/para director, nitration of aniline gives the meta isomer predominantly. Explain this result.

Textbook Question

Predict the major product(s) that would result when molecules (a)–(i) are allowed to react under the following conditions. (iv) chlorocyclopentane, AlCl₃, (v) 1-chloro-1-methylcyclohexane , AlCl₃, (vi) PhCOCl, AlCl₃. If no reaction will occur, indicate by writing NR.

(a)

Textbook Question

Predict the products of the following electrophilic aromatic substitution reactions.

(b)

Textbook Question

Would you expect chlorination to occur ortho, para, or meta to the pyridinium ion in the following molecule? Explain your answer.

Textbook Question

Protonation of aniline slows electrophilic aromatic substitution and directs electrophiles to the meta position. Why?

Textbook Question

Predict the product of the following Friedel–Crafts acylation reactions.

(b)

Textbook Question

Predict the major product of the following electrophilic aromatic substitution reactions.

(c)

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Predict the major product of the following electrophilic aromatic substitution reactions.(c)

Key Concepts

Electrophilic Aromatic Substitution (EAS)

Directing Effects of Substituents

Reactivity and Orientation in EAS

Watch next

Predict the major product of the following electrophilic aromatic substitution reactions.
(c)