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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4:51 minutes

Problem 17c

Textbook Question

Predict the products (if any) of the following reactions.
a. (excess) benzene + isobutyl chloride + AlCl₃

Verified step by step guidance

Step 1: Recognize the reaction type. This is a Friedel-Crafts alkylation reaction, where an alkyl halide reacts with an aromatic compound (benzene) in the presence of a Lewis acid catalyst (AlCl3 or FeCl3).

Step 2: Understand the role of the catalyst. FeCl3 acts as a Lewis acid, accepting a lone pair from the chlorine atom in isobutyl chloride, forming a carbocation intermediate.

Step 3: Analyze the carbocation formation. Isobutyl chloride forms a primary carbocation initially, but due to carbocation rearrangement, it will rearrange to a more stable tertiary carbocation.

Step 4: Predict the electrophilic substitution. The tertiary carbocation acts as the electrophile and reacts with benzene, leading to the formation of an alkylbenzene product. The benzene ring donates electrons to the carbocation, forming a sigma complex, which then loses a proton to restore aromaticity.

Step 5: Consider the excess benzene. Since benzene is in excess, the reaction will likely produce a mono-substituted product (tert-butylbenzene) rather than polysubstitution, as steric hindrance prevents further substitution.

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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 fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this process, the aromatic system retains its stability while allowing for the introduction of new substituents. The reaction typically involves the formation of a sigma complex, followed by deprotonation to restore aromaticity.

Lewis Acids and Catalysis

Lewis acids, such as AlCl3, are compounds that can accept an electron pair from a Lewis base, facilitating reactions by generating more reactive electrophiles. In the context of EAS, AlCl3 activates alkyl halides like isobutyl chloride, allowing them to form a more potent electrophile that can effectively react with the aromatic ring. This catalytic role is crucial for enhancing the reaction rate and product yield.

Regioselectivity in Substitution Reactions

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In EAS reactions, the nature of the substituents already present on the aromatic ring influences where new substituents will attach. For example, alkyl groups are generally ortho/para-directing, meaning they favor substitution at the ortho or para positions relative to themselves.

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Textbook Question

Give the products, if any, of each of the following reactions:

a. benzonitrile + methyl chloride + AlCl₃

b. phenol + Br₂

Textbook Question

Give the products, if any, of each of the following reactions:

c. benzoic acid + CH₃CH₂Cl + AlCl₃

d. benzene + 2 CH₃Cl + AlCl₃

Textbook Question

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

(g) 1-chloro-2,2-dimethylpropane + AlCl₃

Textbook Question

Propose products (if any) and mechanisms for the following AlCl₃-catalyzed reactions:

c. 3-chloro-2,2-dimethylbutane with isopropylbenzene

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

(h) benzoyl chloride + AlCl₃

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