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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4:41 minutes

Problem 50h

Textbook Question

Predict the major products formed when benzene reacts (just once) with the following reagents.
(h) benzoyl chloride + AlCl₃

Verified step by step guidance

Recognize that the reaction involves benzene and benzoyl chloride in the presence of AlCl₃, which is a Friedel-Crafts acylation reaction. This reaction introduces an acyl group onto the benzene ring.

Understand the role of AlCl₃ as a Lewis acid catalyst. It reacts with benzoyl chloride (C₆H₅COCl) to generate the acylium ion (C₆H₅CO⁺), which is the electrophile in this reaction.

Write the mechanism: The acylium ion (C₆H₅CO⁺) is formed when AlCl₃ coordinates with the chlorine atom of benzoyl chloride, causing the Cl to leave as AlCl₄⁻.

Show the electrophilic aromatic substitution (EAS) step: The benzene ring donates a pair of π-electrons to the acylium ion, forming a resonance-stabilized carbocation intermediate.

Conclude the reaction: The intermediate loses a proton (H⁺), and the aromaticity of the benzene ring is restored. The major product is benzophenone (C₆H₅COC₆H₆), and AlCl₃ is regenerated in the process.

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Key Concepts

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

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 this process, the aromatic system retains its stability and aromaticity, making it a key reaction for modifying aromatic compounds. Understanding EAS is crucial for predicting the products of reactions involving benzene and electrophiles.

Friedel-Crafts Acylation

Friedel-Crafts acylation is a specific type of electrophilic aromatic substitution where an acyl group is introduced into an aromatic ring using an acyl chloride and a Lewis acid catalyst, such as AlCl3. This reaction results in the formation of ketones and is significant for synthesizing aromatic ketones. Recognizing this reaction helps in predicting the product when benzene reacts with benzoyl chloride.

Role of Lewis Acids

Lewis acids, such as AlCl3, are substances that can accept an electron pair from a Lewis base to form a coordinate covalent bond. In the context of Friedel-Crafts reactions, the Lewis acid activates the acyl chloride, generating a more reactive electrophile that can effectively attack the aromatic ring. Understanding the role of Lewis acids is essential for grasping how they facilitate electrophilic aromatic substitution reactions.

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Related Practice

Textbook Question

Predict the products (if any) of the following reactions.

a. (excess) benzene + isobutyl chloride + AlCl₃

Textbook Question

Predict the products (if any) of the following reactions.

b. (excess) toluene + butan-1-ol + BF₃

Textbook Question

Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.

(d) Reagents: benzamide (PhCONH₂) + CH₃CH₂Cl

Desired Product: p-ethylbenzamide

Textbook Question

(e) Reagents: toluene + HNO₃, H₂SO₄, heat

Desired Product: 2,4,6-trinitrotoluene (TNT)

Textbook Question

Predict the product(s) of the following reactions.

(d)

Textbook Question

Predict the major products formed when benzene reacts (just once) with the following reagents.

e. isobutylene + HF

Textbook Question