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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5:04 minutes

Problem 53b

Textbook Question

Predict the major products of the following reactions.
(b) phenol + tert-butyl chloride + AlCl₃

Verified step by step guidance

Step 1: Recognize the type of reaction. This is an example of a Friedel-Crafts alkylation reaction, where an aromatic compound (phenol) reacts with an alkyl halide (tert-butyl chloride) in the presence of a Lewis acid catalyst (AlCl₃). The reaction introduces an alkyl group onto the aromatic ring.

Step 2: Understand the role of the reagents. AlCl₃ acts as a Lewis acid to generate a carbocation from tert-butyl chloride. The tert-butyl carbocation (C(CH₃)₃⁺) is a highly stable tertiary carbocation, which will act as the electrophile in this reaction.

Step 3: Consider the directing effects of the hydroxyl (-OH) group on phenol. The -OH group is an activating and ortho/para-directing group, meaning it increases the reactivity of the aromatic ring and directs the incoming electrophile to the ortho and para positions relative to itself.

Step 4: Predict the major products. The tert-butyl group will preferentially add to the para position of the phenol due to steric hindrance at the ortho positions. However, some ortho substitution may also occur as a minor product.

Step 5: Draw the structures of the products. The major product will be para-tert-butylphenol, and the minor product will be ortho-tert-butylphenol. Ensure to represent the aromatic ring with the hydroxyl group and the tert-butyl group in the correct positions.

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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 the case of phenol, the hydroxyl group (-OH) activates the ring, making it more reactive towards electrophiles. Understanding EAS is crucial for predicting the products of reactions involving aromatic compounds.

Lewis Acids and Bases

Lewis acids are species that can accept an electron pair, while Lewis bases donate an electron pair. In this reaction, AlCl3 acts as a Lewis acid, facilitating the formation of a more reactive electrophile from tert-butyl chloride. Recognizing the role of Lewis acids and bases is essential for understanding how they influence reaction mechanisms and product formation.

Regioselectivity in Substitution Reactions

Regioselectivity refers to the preference of a chemical reaction to occur at one location over another in a molecule. In the case of phenol reacting with tert-butyl chloride in the presence of AlCl3, the reaction will likely occur at the ortho or para positions due to the activating effect of the hydroxyl group. Understanding regioselectivity helps predict the major products formed in substitution reactions.

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Textbook Question

b. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.

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For each horizontal row of substituted benzenes, indicate

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Predict the major products of the following reactions.(b) phenol + tert-butyl chloride + AlCl3

Key Concepts

Electrophilic Aromatic Substitution

Lewis Acids and Bases

Regioselectivity in Substitution Reactions

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Predict the major products of the following reactions.
(b) phenol + tert-butyl chloride + AlCl₃