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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Problem 81c

Textbook Question

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)

Verified step by step guidance

Identify the organometallic reagent involved in the reaction. Organometallic compounds typically have a carbon-metal bond, where the carbon is more electronegative and carries a partial negative charge, acting as a nucleophile.

Recognize the epoxide structure in the reaction. Epoxides are three-membered cyclic ethers with significant ring strain, making them reactive towards nucleophiles.

Determine the site of nucleophilic attack. The nucleophile (carbon from the organometallic) will attack the less hindered carbon atom of the epoxide, leading to the opening of the epoxide ring.

Consider the stereochemistry of the reaction. The nucleophilic attack on the epoxide will occur from the opposite side of the leaving group (oxygen), resulting in an inversion of configuration at the carbon center being attacked.

Predict the final product. The result of the nucleophilic attack and ring opening will be an alcohol, where the oxygen from the epoxide becomes a hydroxyl group, and the carbon chain from the organometallic reagent is now attached to the former epoxide carbon.

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Key Concepts

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

Organometallic Compounds

Organometallic compounds are chemical species that contain a bond between a carbon atom of an organic molecule and a metal. These compounds are known for their strong nucleophilic properties, allowing them to react with electrophiles, such as epoxides. The reactivity of organometallics is largely due to the ionic character of the carbon-metal bond, which imparts a negative charge to the carbon atom.

Epoxide Reactivity

Epoxides are three-membered cyclic ethers that are highly reactive due to the strain in their ring structure. They can undergo nucleophilic attack at the carbon atoms, which are electrophilic due to the ring strain. When a strong nucleophile, like an organometallic compound, attacks an epoxide, it typically opens the ring, leading to the formation of a more stable product.

Nucleophilic Substitution Mechanism

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a substrate. In the context of organometallics reacting with epoxides, the nucleophile attacks the less hindered carbon atom of the epoxide, resulting in the opening of the ring and the formation of an alcohol. Understanding this mechanism is crucial for predicting the products of such reactions.

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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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Predict the product of the following epoxide addition reactions.

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

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

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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.

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