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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Problem 81b

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.]
(b)

Verified step by step guidance

Identify the organometallic reagent in the reaction. Organometallic compounds typically have a carbon-metal bond, where the carbon is nucleophilic due to its partial negative charge.

Recognize the epoxide as the electrophile in the reaction. Epoxides are three-membered cyclic ethers with significant ring strain, making them highly reactive toward nucleophiles.

Determine the site of nucleophilic attack. The nucleophile (carbon from the organometallic reagent) will attack the less sterically hindered carbon of the epoxide, leading to ring opening. This is due to the SN2-like mechanism of the reaction.

Add a protonation step. After the nucleophilic attack and ring opening, the negatively charged oxygen (from the epoxide) will be protonated by a suitable proton source (e.g., water or an acid) to form the final alcohol product.

Draw the final product. The product will be an alcohol where the nucleophile has added to the less hindered carbon of the epoxide, and the oxygen from the epoxide is now part of a hydroxyl group.

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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 molecules that contain a bond between a carbon atom of an organic group and a metal. These compounds are known for their strong nucleophilic properties, allowing them to react with electrophiles, such as epoxides. The metal can vary, influencing the reactivity and stability of the compound.

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 less hindered carbon atom, leading to ring-opening reactions. Understanding the mechanism of this reaction is crucial for predicting the products formed when epoxides react with nucleophiles.

Ionic Carbon-Metal Bond

In the context of organometallics, assuming an ionic carbon-metal bond means that the carbon atom carries a negative charge, making it a strong nucleophile. This assumption simplifies the analysis of the reaction mechanism, as it allows for straightforward predictions about how the nucleophile will interact with the electrophilic epoxide, leading to the formation of specific products.