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

10. Addition Reactions

Epoxide Reactions

Organic Chemistry

10. Addition Reactions

Epoxide Reactions

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3:10 minutes

Problem 80b

Textbook Question

Predict the product of the following epoxide addition reactions.
(b)

Verified step by step guidance

Identify the structure of the epoxide and the reagents involved in the reaction. Epoxides are three-membered cyclic ethers, and their reactions often involve nucleophilic attack.

Determine the type of reaction mechanism. Epoxide ring-opening reactions can proceed via either acid-catalyzed or base-catalyzed mechanisms, depending on the conditions provided.

For an acid-catalyzed mechanism, the epoxide oxygen is protonated, making the epoxide more electrophilic. The nucleophile then attacks the more substituted carbon due to the partial positive charge developed there.

For a base-catalyzed mechanism, the nucleophile directly attacks the less hindered carbon of the epoxide, leading to ring opening. This is because the nucleophile is strong and the reaction is under kinetic control.

Draw the structure of the product, ensuring that the stereochemistry is correctly represented. Consider any stereochemical implications of the reaction, such as inversion of configuration at the carbon where the nucleophile attacks.

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Key Concepts

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

Epoxide Structure

Epoxides are three-membered cyclic ethers characterized by a highly strained ring structure. This strain makes them reactive intermediates in organic reactions, particularly in nucleophilic addition reactions. Understanding the geometry and reactivity of epoxides is crucial for predicting the products of their reactions.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic center, leading to the formation of new bonds. In the case of epoxides, nucleophiles can open the strained ring, resulting in the formation of alcohols or other functional groups. The nature of the nucleophile and the reaction conditions can significantly influence the outcome.

Stereochemistry of Reactions

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In epoxide addition reactions, the stereochemistry of the reactants and the nucleophile's approach can lead to different stereochemical outcomes in the products. Understanding stereochemical principles is essential for predicting the configuration of the final products.

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Related Practice

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.

a. 2,2-dimethylxirane + H⁺/H₂¹⁸O (oxygen labeled water)

b. 2,2-dimethylxirane + H¹⁸O^–/H₂¹⁸O (oxygen labeled water)

Textbook Question

Predict the major product when each reagent reacts with ethylene oxide.

(a) NaOCH₂CH₃ (sodium ethoxide)

(b) NaNH₂ (sodium amide)

Textbook Question

Predict the products of the following reactions.

(m)

(n)

Textbook Question

Working backward, design a synthesis of the following alcohol using two different epoxide/Grignard reagent combinations.

Textbook Question

Predict the product of the following epoxide addition reactions.

(a)

Textbook Question

In Chapter 13, we learned that epoxide opening can give different products, depending on whether the reaction occurs under acidic or basic conditions. Explain why the epoxide shown opens identically under either set of conditions.

Textbook Question

In Chapter 13, we discuss the ring-opening reactions of epoxides, such as the one shown here.

(a) Based on the bonds formed and the bonds broken, calculate ∆H°.

Textbook Question

Chapter 8 discussed the synthesis of cholesterol, which proceeds by a cationic cyclization cascade. Without looking back, suggest a mechanism by which the following reaction occurs. [The carbons have been numbered for you.]

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Predict the product of the following epoxide addition reactions.(b)

Key Concepts

Epoxide Structure

Nucleophilic Addition

Stereochemistry of Reactions

Watch next

Predict the product of the following epoxide addition reactions.
(b)