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:Any Carbocation Mechanism

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Any Carbocation Mechanism

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Problem 79b

Textbook Question

Propose a mechanism for each of the following reactions:
b.

Verified step by step guidance

Identify the type of reaction taking place. For example, determine if it is a substitution, elimination, addition, or rearrangement reaction. This will help guide the mechanism.

Analyze the reactants and reagents provided. Look for functional groups, leaving groups, nucleophiles, electrophiles, or catalysts that might influence the reaction pathway.

Determine the first step of the mechanism. For instance, if the reaction involves a nucleophile and an electrophile, the nucleophile will attack the electrophile, forming a new bond. Represent this step using curved arrows to show electron movement.

Continue the mechanism step by step, ensuring that each intermediate is stable or reasonable. For example, if a carbocation intermediate forms, consider whether rearrangement or resonance stabilization might occur.

Conclude the mechanism by showing the final product and regenerating any catalysts if applicable. Ensure that all charges are balanced and that the electron flow is consistent throughout the mechanism.

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Key Concepts

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

Reaction Mechanisms

A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. It outlines the sequence of elementary steps, including bond breaking and formation, and the intermediates formed during the reaction. Understanding mechanisms is crucial for predicting the outcome of reactions and for designing new synthetic pathways.

Types of Organic Reactions

Organic reactions can be classified into several types, including substitution, addition, elimination, and rearrangement reactions. Each type has distinct characteristics and mechanisms. Recognizing the type of reaction helps in predicting the behavior of reactants and the nature of the products formed.

Curved Arrow Notation

Curved arrow notation is a visual representation used in organic chemistry to depict the movement of electrons during a reaction. Arrows indicate the direction of electron flow, showing how bonds are broken and formed. Mastery of this notation is essential for accurately illustrating and understanding reaction mechanisms.

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Related Practice

Textbook Question

Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl₃.

a. What are the major and minor products of the following reaction?

b. Would you expect epoxides to undergo similar reactions?

Textbook Question

Propose a mechanism for each of the following reactions:

Textbook Question

Phenolphthalein, a common nonprescription laxative, is also an acid–base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

a. Propose a mechanism for the synthesis of phenolphthalein.

Textbook Question

What are the products of the following reactions?b.

Textbook Question

Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl₃.

a. What are the major and minor products of the following reaction?

b. Would you expect epoxides to undergo similar reactions?

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