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 33a

Textbook Question

Predict the product of the diorganocuprate cross-coupling reactions shown.
(a)

Verified step by step guidance

Identify the reactants involved in the diorganocuprate cross-coupling reaction. Typically, these reactions involve an organocuprate reagent (R2CuLi) and an organic halide (R'-X).

Understand the role of the organocuprate reagent. In this reaction, the organocuprate acts as a nucleophile, where one of the organic groups (R) will be transferred to the organic halide.

Determine the leaving group in the organic halide. The halide (X) is the leaving group, which will be replaced by the organic group from the organocuprate.

Predict the product by coupling the organic group from the organocuprate with the organic group from the halide. The new bond formed will be between the carbon of the organocuprate and the carbon of the organic halide.

Consider any stereochemical or regiochemical outcomes. If the organic halide is chiral or has multiple reactive sites, consider how the reaction conditions might affect the stereochemistry or regioselectivity of the product.

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Key Concepts

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

Diorganocuprate Reagents

Diorganocuprate reagents, also known as Gilman reagents, are organocopper compounds typically represented as R2CuLi. They are used in organic synthesis for forming carbon-carbon bonds through nucleophilic substitution reactions. These reagents are particularly useful for coupling with alkyl, aryl, or vinyl halides to form new carbon-carbon bonds, often with high selectivity and mild reaction conditions.

Cross-Coupling Reactions

Cross-coupling reactions are a class of reactions where two different organic groups are joined together with the aid of a metal catalyst. In the context of diorganocuprate reagents, these reactions involve the coupling of an organocuprate with an organic halide to form a new carbon-carbon bond. The reaction typically proceeds through a mechanism involving oxidative addition, transmetalation, and reductive elimination, resulting in the formation of the desired coupled product.

Reaction Mechanism

Understanding the mechanism of diorganocuprate cross-coupling is crucial for predicting the reaction product. The mechanism generally involves the oxidative addition of the organic halide to the copper center, followed by transmetalation where the organic group from the cuprate is transferred to the metal center. Finally, reductive elimination occurs, forming the new carbon-carbon bond and regenerating the copper catalyst. This sequence ensures the selective formation of the desired product.

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Related Practice

Textbook Question

Starting with cyclohexane, how could the following compounds be prepared?

Textbook Question

A chemist attempted the reaction below, one we introduce in Chapter 17, expecting the reaction between a strong nucleophile and a ketone in water to give an alkoxide product.

(a) Why did the reaction fail?

(b) How could the reaction conditions be changed to give a successful reaction?

Textbook Question

Give the expected products of the following reactions. Include a protonation step where necessary.

(a) 2,2-dimethyloxirane + isopropylmagnesium bromide

(b) propylene oxide + n-butyllithium

Textbook Question

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Textbook Question

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

(b)

Textbook Question