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 33c

Textbook Question

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

Verified step by step guidance

Identify the reagents involved in the reaction. The diorganocuprate reagent is a lithium cuprate, specifically a (methoxyphenyl)2CuLi, and the substrate is a phenyl-substituted acyl chloride.

Understand the mechanism of the diorganocuprate reaction. Diorganocuprates are known for their ability to perform nucleophilic substitution reactions, particularly with acyl chlorides, leading to the formation of ketones.

Recognize the role of the cuprate reagent. In this reaction, one of the methoxyphenyl groups from the cuprate will act as a nucleophile and attack the carbonyl carbon of the acyl chloride, displacing the chloride ion.

Predict the structure of the product. The methoxyphenyl group will replace the chlorine atom in the acyl chloride, forming a new carbon-carbon bond and resulting in a ketone with a methoxyphenyl substituent.

Consider stereochemistry and regiochemistry. Since the reaction involves a straightforward nucleophilic acyl substitution, stereochemistry is not a concern here, and the regiochemistry is determined by the position of the acyl chloride group.

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Key Concepts

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

Diorganocuprate Reagents

Diorganocuprates are organometallic compounds containing copper, typically represented as R2CuLi, where R is an organic group. They are used in cross-coupling reactions to form carbon-carbon bonds by transferring an organic group to an electrophile. Understanding their reactivity and how they interact with various substrates is crucial for predicting the products of these reactions.

Cross-Coupling Reactions

Cross-coupling reactions are a class of reactions in organic chemistry where two different organic groups are joined together, typically facilitated by a metal catalyst. These reactions are essential for forming complex organic molecules and are widely used in the synthesis of pharmaceuticals and materials. Familiarity with the mechanisms and conditions of these reactions is vital for predicting the outcome of diorganocuprate reactions.

Electrophiles and Nucleophiles

In organic chemistry, electrophiles are species that accept electron pairs from nucleophiles, which are electron-rich species that donate electron pairs. The interaction between these two types of species is fundamental in many reactions, including cross-coupling. Identifying the electrophile in the reaction and understanding its reactivity with the nucleophilic diorganocuprate is essential for predicting the final product.

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