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 Alkylation Mechanism

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Friedel-Crafts Alkylation Mechanism

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2:46 minutes

Problem 60e

Textbook Question

Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the 1-position. Predict the major products of the reactions of naphthalene with the following reagents.

(e) cyclohexanol and BF₃

Verified step by step guidance

Step 1: Understand the reaction type. The problem involves electrophilic aromatic substitution, which is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. Naphthalene is the aromatic compound in this case.

Step 2: Identify the reagents. Cyclohexanol and BF3 are provided as reagents. BF3 acts as a Lewis acid, which can activate cyclohexanol to form a carbocation. This carbocation will serve as the electrophile in the reaction.

Step 3: Determine the site of substitution. In naphthalene, the alpha position (1-position) is more reactive due to its higher electron density and stability of the intermediate carbocation formed during the reaction. Thus, substitution is expected to occur at the alpha position.

Step 4: Predict the product formation. The carbocation generated from cyclohexanol will attack the alpha position of naphthalene, leading to the formation of a new bond between the naphthalene ring and the cyclohexyl group.

Step 5: Consider resonance stabilization. After the electrophilic attack, the intermediate formed will undergo resonance stabilization, ensuring the aromaticity of the naphthalene ring is restored in the final product.

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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. This reaction is crucial for modifying aromatic compounds, allowing for the introduction of various functional groups. The mechanism involves the formation of a sigma complex, where the aromaticity is temporarily lost, followed by deprotonation to restore aromaticity.

Naphthalene Structure and Reactivity

Naphthalene is a polycyclic aromatic hydrocarbon consisting of two fused benzene rings. Its structure allows for electrophilic substitution primarily at the 1-position (α position) and 2-position (β position). The reactivity of naphthalene is influenced by its electron-rich nature, making it susceptible to electrophiles, with the α position being favored due to steric and electronic factors.

Role of Lewis Acids in EAS

Lewis acids, such as BF3, are often used in electrophilic aromatic substitution reactions to enhance the electrophilicity of the reacting species. In the presence of a Lewis acid, the electrophile can become more reactive, facilitating the substitution process. This is particularly important when the electrophile is weak, as the Lewis acid can stabilize the transition state and promote the reaction.

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Related Practice

Textbook Question

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

b. methyl chloride with anisole

Textbook Question

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

a. tert-butyl bromide, AlCl₃

b. 1-chlorobutane, AlCl₃

Textbook Question

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

c. isobutyl alcohol + BF₃

Textbook Question

Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with the following reagents.

(d) isobutylene and HF

Textbook Question

For each reaction, show the generation of the electrophile and predict the products.

c. tert-butylbenzene + 2-methylpropene + HF

Textbook Question

For each reaction, show the generation of the electrophile and predict the products.

d. propan-2-ol + toluene + BF₃

Textbook Question

Predict the product of the following Friedel–Crafts alkylation reactions. Assume only one alkyl group adds in each case.

(d)

Textbook Question

What is the major product of a Friedel–Crafts alkylation using the following alkyl chlorides?

e. (CH₃)₂CHCH₂Cl

f. CH₂=CHCH₂Cl

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Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the 1-position. Predict the major products of the reactions of naphthalene with the following reagents.(e) cyclohexanol and BF3

Key Concepts

Electrophilic Aromatic Substitution (EAS)

Naphthalene Structure and Reactivity

Role of Lewis Acids in EAS

Watch next

Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the 1-position. Predict the major products of the reactions of naphthalene with the following reagents.

(e) cyclohexanol and BF₃