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

EAS:Friedel-Crafts Acylation Mechanism

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Friedel-Crafts Acylation Mechanism

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2:34 minutes

Problem 18

Textbook Question

What are the products of the following reactions?c.

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Step 1: Recognize the reaction type. This is a Friedel-Crafts acylation reaction, where an aromatic compound reacts with an acyl chloride in the presence of a Lewis acid catalyst (AlCl₃).

Step 2: Identify the reactants. The aromatic compound is benzene, and the acyl chloride is benzoyl chloride (C₆H₅COCl). The catalyst is aluminum chloride (AlCl₃).

Step 3: Understand the mechanism. The AlCl₃ catalyst interacts with the acyl chloride to form a highly electrophilic acylium ion (C₆H₅CO⁺), which is the active species in the reaction.

Step 4: Predict the electrophilic aromatic substitution. The acylium ion attacks the benzene ring, leading to the formation of a new carbon-carbon bond. This results in the substitution of a hydrogen atom on the benzene ring with the acyl group (C₆H₅CO).

Step 5: Finalize the product. The product of this reaction is acetophenone (C₆H₅COC₆H₆), where the benzene ring is bonded to the carbonyl group of the acyl chloride. The AlCl₃ catalyst is regenerated at the end of the reaction.

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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 an electrophilic aromatic substitution reaction where an acyl group is introduced into an aromatic ring. This reaction typically involves the use of an acyl chloride and a Lewis acid catalyst, such as aluminum chloride (AlCl3), which activates the acyl chloride to form a more reactive acylium ion. The acylium ion then reacts with the aromatic compound, resulting in the formation of a ketone substituted on the aromatic ring.

Electrophilic Aromatic Substitution (EAS)

Electrophilic aromatic substitution is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. The aromatic system's electron-rich nature allows it to react with electrophiles, leading to the formation of a new carbon-electrophile bond. This mechanism is crucial for understanding various reactions involving aromatic compounds, including Friedel-Crafts reactions.

Role of Lewis Acids

Lewis acids are substances that can accept an electron pair from a Lewis base, facilitating various chemical reactions. In the context of Friedel-Crafts acylation, aluminum chloride (AlCl3) acts as a Lewis acid by coordinating with the acyl chloride, enhancing its electrophilicity. This interaction is essential for generating the acylium ion, which is the active electrophile that reacts with the aromatic compound.

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