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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2:47 minutes

Problem 16d

Textbook Question

For each reaction, show the generation of the electrophile and predict the products.
d. propan-2-ol + toluene + BF₃

Verified step by step guidance

Step 1: Understand the role of BF₃ in the reaction. Boron trifluoride (BF₃) is a Lewis acid, meaning it can accept electron pairs. In this reaction, BF₃ will likely interact with propan-2-ol to generate an electrophile.

Step 2: Analyze the interaction between BF₃ and propan-2-ol. Propan-2-ol contains a hydroxyl (-OH) group, which has lone pairs of electrons. BF₃ can coordinate with these lone pairs, leading to the formation of a complex that enhances the electrophilic character of the carbon atom attached to the hydroxyl group.

Step 3: Consider the role of toluene in the reaction. Toluene is an aromatic compound with a methyl group attached to a benzene ring. The aromatic ring can act as a nucleophile due to its π-electrons, which can interact with the electrophile generated in Step 2.

Step 4: Predict the product formation. The electrophile generated from propan-2-ol and BF₃ will likely undergo an electrophilic aromatic substitution reaction with toluene. This involves the aromatic ring attacking the electrophile, followed by the restoration of aromaticity.

Step 5: Summarize the reaction mechanism. The reaction proceeds as follows: (1) BF₃ interacts with propan-2-ol to generate an electrophile, (2) the electrophile reacts with the aromatic ring of toluene, and (3) a substituted aromatic product is formed, with the electrophile replacing a hydrogen atom on the benzene ring.

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Key Concepts

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

Electrophiles

Electrophiles are species that accept electron pairs from nucleophiles during chemical reactions. They are typically positively charged or neutral molecules with an electron-deficient atom, making them reactive towards nucleophiles. In the given reaction, BF3 acts as a Lewis acid, generating an electrophile that can react with the nucleophilic propan-2-ol.

Lewis Acids and Bases

Lewis acids are substances that can accept an electron pair, while Lewis bases donate an electron pair. In this reaction, BF3, a Lewis acid, interacts with propan-2-ol, a Lewis base, to form a complex. This interaction is crucial for understanding how the electrophile is generated and how the reaction proceeds.

Electrophilic Substitution Reactions

Electrophilic substitution reactions involve the replacement of a hydrogen atom in an aromatic compound with an electrophile. In this case, toluene undergoes electrophilic substitution after the generation of the electrophile from the interaction of propan-2-ol and BF3. Understanding this mechanism is essential for predicting the products of the reaction.

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Related Practice

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

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

Textbook Question

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

c. tert-butylbenzene + 2-methylpropene + HF

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

Textbook Question

Design a synthesis for each of the following, using an intramolecular reaction:

Textbook Question

What product is obtained from the reaction of excess benzene with each of the following reagents?

c. dichloromethane + AlCl₃

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For each reaction, show the generation of the electrophile and predict the products.d. propan-2-ol + toluene + BF3

Key Concepts

Electrophiles

Lewis Acids and Bases

Electrophilic Substitution Reactions

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For each reaction, show the generation of the electrophile and predict the products.
d. propan-2-ol + toluene + BF₃