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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3:22 minutes

Problem 17b

Textbook Question

Predict the products (if any) of the following reactions.
b. (excess) toluene + butan-1-ol + BF₃

Verified step by step guidance

Step 1: Recognize the reactants and the role of BF3. Toluene is an aromatic compound, butan-1-ol is a primary alcohol, and BF3 (boron trifluoride) is a Lewis acid that can facilitate electrophilic aromatic substitution or other reactions by activating the alcohol.

Step 2: Understand the interaction between BF3 and butan-1-ol. BF3 can coordinate with the oxygen atom of the alcohol, increasing the electrophilicity of the carbon attached to the hydroxyl group. This can lead to the generation of a carbocation intermediate.

Step 3: Consider the reaction mechanism. The carbocation formed from butan-1-ol can act as an electrophile, and the aromatic ring of toluene can act as a nucleophile. Electrophilic aromatic substitution is likely to occur, where the carbocation attacks the aromatic ring.

Step 4: Predict the regioselectivity of the substitution. Toluene has a methyl group that is an electron-donating group, making the ortho and para positions more reactive. The substitution will likely occur at one of these positions.

Step 5: Account for the excess toluene. Since toluene is in excess, multiple substitutions may occur, leading to the formation of di- or tri-substituted products. The final products will depend on the reaction conditions and the stability of intermediates.

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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 in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this reaction, the aromatic compound, such as toluene, acts as a nucleophile, attacking the electrophile. The presence of a Lewis acid like BF3 enhances the electrophilicity of the reactants, facilitating the substitution process.

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 acts as a Lewis acid, coordinating with the alcohol (butan-1-ol) to form a more reactive species. This interaction is crucial for the activation of the alcohol, allowing it to participate in the electrophilic substitution with toluene.

Reactivity of Alcohols

Alcohols can act as nucleophiles in organic reactions, but their reactivity often requires activation, especially in the presence of Lewis acids. In this case, butan-1-ol can be protonated or activated by BF3, making it a better nucleophile. Understanding how alcohols interact with Lewis acids is essential for predicting the products of the reaction involving toluene and butan-1-ol.

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