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 33b

Textbook Question

Predict the product of the following Friedel–Crafts acylation reactions.
(b)

Verified step by step guidance

Identify the acyl chloride in the reaction. In this case, it is a 4-chlorobutanoyl chloride, which will be used in the Friedel-Crafts acylation.

Recognize the role of AlCl₃ as a Lewis acid catalyst. It will facilitate the generation of the acylium ion from the acyl chloride.

Understand that the acylium ion, which is a positively charged species, will be formed by the interaction of the acyl chloride with AlCl₃. This ion is highly electrophilic and will attack the benzene ring.

Predict the site of electrophilic attack on the benzene ring. The acylium ion will preferentially attack the para position relative to any existing substituents, unless steric hindrance or other directing effects are present.

Consider the final product structure. The acyl group will be added to the benzene ring, resulting in a ketone with the acyl group attached to the para position of the benzene ring.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Friedel-Crafts Acylation

Friedel-Crafts acylation is a reaction that introduces an acyl group into an aromatic ring using an acyl chloride and a Lewis acid catalyst, typically aluminum chloride (AlCl3). The reaction proceeds through the formation of an acylium ion, which acts as an electrophile, attacking the electron-rich aromatic ring to form a ketone. This reaction is useful for adding carbonyl groups to aromatic compounds, enhancing their reactivity and functional diversity.

Role of Aluminum Chloride (AlCl3)

Aluminum chloride (AlCl3) is a strong Lewis acid used as a catalyst in Friedel-Crafts reactions. It facilitates the generation of the acylium ion from the acyl chloride by accepting a chloride ion, thus increasing the electrophilicity of the acyl group. This enhanced electrophile can then effectively attack the aromatic ring, leading to the substitution of a hydrogen atom with the acyl group, forming a ketone.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the context of Friedel-Crafts acylation, the acylium ion acts as the electrophile, attacking the π-electron-rich benzene ring. The reaction proceeds through the formation of a resonance-stabilized carbocation intermediate, followed by deprotonation to restore aromaticity, resulting in the acylated aromatic compound.

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