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

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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2:46 minutes

Problem 8a

Textbook Question

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

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Identify the structure of the epoxide. An epoxide is a three-membered cyclic ether with significant ring strain, making it highly reactive toward nucleophiles.

Determine the reaction conditions. If the reaction occurs under acidic conditions, the epoxide will be protonated first, making it more electrophilic. If the reaction occurs under basic or neutral conditions, the nucleophile will directly attack the less substituted carbon of the epoxide due to steric hindrance.

Analyze the regioselectivity of the reaction. Under acidic conditions, the nucleophile typically attacks the more substituted carbon of the epoxide due to the formation of a more stable carbocation-like intermediate. Under basic conditions, the nucleophile attacks the less substituted carbon due to steric factors.

Consider the stereochemistry of the reaction. The nucleophilic attack on the epoxide occurs via an SN2 mechanism, leading to an inversion of configuration at the carbon being attacked.

Draw the product of the reaction by opening the epoxide ring and attaching the nucleophile to the appropriate carbon, ensuring that the stereochemistry and regioselectivity are consistent with the reaction conditions.

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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 chemistry, allowing them to undergo various nucleophilic addition reactions. Understanding the geometry and reactivity of epoxides is crucial for predicting the outcomes 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, the nucleophile typically opens the strained ring, resulting in the formation of a diol or other products depending on the nature of the nucleophile and reaction conditions.

Regioselectivity and Stereochemistry

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereochemistry involves the spatial arrangement of atoms in molecules. In epoxide addition reactions, the choice of nucleophile and reaction conditions can influence both the regioselectivity and stereochemistry of the product, making it essential to consider these factors when predicting the outcome.

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Using the epoxide shown, addition of an organolithium reagent, when followed by an acid quench, produces only the starting epoxy alcohol. Why? How could the reaction be modified to produce the desired molecule? [Hint: Look back at Section 13.14.]

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A variety of organometallics, which as strong nucleophiles can react with epoxides, are introduced in Chapter 16. Predict the product of these reactions. [Hint: Assume the carbon–metal bond in each is ionic, with the carbon possessing the negative charge.]

(c)

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Give the structures of intermediates A through H in the following synthesis of trans-1-cyclohexyl-2-methoxycyclohexane.

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(o)

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For each of the following carbonyl addition reactions, would you expect a racemic mixture or a mixture enriched in one stereoisomer? In each case, draw both possible stereoisomeric products.

(a)

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

Key Concepts

Epoxide Structure

Nucleophilic Addition

Regioselectivity and Stereochemistry

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