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 43b

Textbook Question

Predict the products of the following electrophilic aromatic substitution reactions.
(b)

Verified step by step guidance

Identify the type of reaction: The reaction shown is an electrophilic aromatic substitution (EAS) where a sulfonation reaction is taking place. The reagents SO3 and H2SO4 are used to introduce a sulfonic acid group (SO3H) onto the aromatic ring.

Determine the directing effects of substituents: The acyl group (C=O) attached to the benzene ring is a meta-directing group due to its electron-withdrawing nature. This means that the incoming electrophile (SO3) will preferentially add to the meta position relative to the acyl group.

Draw the intermediate: The electrophile, SO3, will attack the benzene ring at the meta position, forming a sigma complex (arenium ion) where the positive charge is delocalized over the ring.

Reform the aromatic system: The loss of a proton from the sigma complex will restore the aromaticity of the benzene ring, resulting in the formation of the sulfonated product.

Predict the final product: The final product will be a benzene ring with a sulfonic acid group (SO3H) at the meta position relative to the acyl group, due to the directing effects of the acyl 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 one of its hydrogen atoms 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 proceeds through two main steps: the formation of the arenium ion and the subsequent deprotonation to restore aromaticity.

Sulfonation Reaction

Sulfonation is a type of electrophilic aromatic substitution where sulfur trioxide (SO3) acts as the electrophile, often in the presence of sulfuric acid (H2SO4) to form the sulfonic acid group (-SO3H) on the aromatic ring. This reaction is reversible and is used to introduce sulfonic acid groups into aromatic compounds, which can influence the compound's solubility and reactivity.

Directing Effects of Substituents

In EAS reactions, substituents already present on the aromatic ring can influence the position where new groups are added. Electron-withdrawing groups, like the carbonyl group in an acyl group, typically direct incoming electrophiles to the meta position relative to themselves. This is due to their ability to stabilize the arenium ion intermediate through resonance and inductive effects, affecting the regioselectivity of the reaction.

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Related Practice

Textbook Question

Are the following substituents ortho–para directors or meta directors?

a. CH=CHC≡N

b. NO₂

c. CH₂OH

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 major product of the following electrophilic aromatic substitution reactions.

(c)

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)

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Predict the products of the following electrophilic aromatic substitution reactions.(b)

Key Concepts

Electrophilic Aromatic Substitution (EAS)

Sulfonation Reaction

Directing Effects of Substituents

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Predict the products of the following electrophilic aromatic substitution reactions.
(b)