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

13. Alcohols and Carbonyl Compounds

Grignard Reaction

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Grignard Reaction

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3:35 minutes

Problem 36b

Textbook Question

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

Verified step by step guidance

Identify the structure of the epoxide. An epoxide is a cyclic ether with a three-membered ring, typically consisting of two carbon atoms and one oxygen atom.

Determine the conditions of the reaction. Epoxide opening can occur under acidic or basic conditions, which will influence the regioselectivity and stereochemistry of the product.

If the reaction is under acidic conditions, the nucleophile will attack the more substituted carbon atom due to the formation of a more stable carbocation intermediate. If under basic conditions, the nucleophile will attack the less substituted carbon atom due to direct SN2 attack.

Consider the stereochemistry of the reaction. Epoxide opening reactions often result in inversion of configuration at the carbon atom where the nucleophile attacks, due to the backside attack characteristic of SN2 reactions.

Draw the product of the reaction, ensuring to show the correct regioselectivity and stereochemistry based on the conditions provided. Include any additional substituents or groups that may be present in the reaction.

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Key Concepts

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

Epoxide Structure and Reactivity

Epoxides are three-membered cyclic ethers with significant ring strain, making them highly reactive. The strained ring is prone to nucleophilic attack, leading to ring opening. Understanding the structure and reactivity of epoxides is crucial for predicting the outcome of their reactions, as the nucleophile will typically attack the less hindered carbon atom in the ring.

Regioselectivity in Epoxide Opening

Regioselectivity refers to the preference for a chemical reaction to occur at one direction or position over others. In epoxide opening, the regioselectivity is influenced by the nature of the nucleophile and the reaction conditions. Under acidic conditions, the nucleophile attacks the more substituted carbon, while under basic conditions, it attacks the less substituted carbon, affecting the final product.

Stereochemistry of Epoxide Opening

Stereochemistry involves the spatial arrangement of atoms in molecules and its impact on chemical reactions. In epoxide opening, the stereochemistry of the starting material and the reaction conditions determine the stereochemical outcome. The nucleophilic attack typically occurs from the opposite side of the leaving group, leading to an inversion of configuration at the carbon center, which is crucial for predicting the stereochemistry of the product.

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Predict the product of the diorganocuprate cross-coupling reactions shown.

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Predict the product of the diorganocuprate cross-coupling reactions shown.

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Predict the product of the following epoxide opening reactions.

(a)

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(a) Suggest a reason why this reaction did not work as written.

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