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 47b

Textbook Question

Predict the product of the following reactions.
(b)

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Identify the type of reaction: The image shows a reaction between an acyl chloride and a lithium diorganocuprate (Gilman reagent). This is a nucleophilic acyl substitution reaction.

Understand the role of the Gilman reagent: Lithium diorganocuprates are used to perform conjugate additions to α,β-unsaturated carbonyl compounds or to replace halides with alkyl groups.

Analyze the structure of the acyl chloride: The acyl chloride has a five-membered ring with a chlorine atom attached to the carbonyl carbon. This is the site where the nucleophilic attack will occur.

Predict the nucleophilic attack: The Gilman reagent will attack the carbonyl carbon, replacing the chlorine atom with the cyclopropyl group from the reagent.

Consider stereochemistry: Since the reaction involves a cyclic structure, consider any stereochemical implications of the nucleophilic substitution, ensuring the correct orientation of substituents in the final product.

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Key Concepts

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

Organocuprate Reagents

Organocuprate reagents, such as the one depicted with copper and lithium, are used in organic synthesis for nucleophilic substitution reactions. They are particularly effective in replacing halides like chlorine with carbon-based groups. In this reaction, the organocuprate will likely facilitate the substitution of the chlorine atom with the cyclopropyl group, leading to the formation of a new carbon-carbon bond.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism where a nucleophile replaces a leaving group in a molecule. In the given reaction, the chlorine atom acts as the leaving group, and the organocuprate reagent serves as the nucleophile. This process is crucial for forming new carbon-carbon bonds, which is a common goal in organic synthesis.

Stereochemistry in Reactions

Stereochemistry involves the spatial arrangement of atoms in molecules and its impact on chemical reactions. In the provided reaction, the stereochemistry of the reactants and the product must be considered, especially since the reactant contains a chiral center. The configuration of the product will depend on the stereochemical course of the nucleophilic substitution, which can influence the reaction's outcome and the properties of the product.

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Related Practice

Textbook Question

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

(c)

Textbook Question

Suggest a synthesis of the following molecule starting with the reagents shown, using cuprate cross-coupling as the key step.

Textbook Question

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(d)

Textbook Question

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(b)

Textbook Question

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(c)

Textbook Question

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(c)

Textbook Question

To this point, we have seen four reactions that can be done by Gilman reagents. What are they? What do they have in common?

Textbook Question

Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.

(b)

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Predict the product of the following reactions.(b)

Key Concepts

Organocuprate Reagents

Nucleophilic Substitution

Stereochemistry in Reactions

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Predict the product of the following reactions.
(b)