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

25. Condensation Chemistry

Conjugate Addition

Organic Chemistry

25. Condensation Chemistry

Conjugate Addition

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4:10 minutes

Problem 46b

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.
(b)

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Identify the target molecule as a cyclohexanone derivative with a cyclopropyl group attached at the beta position relative to the carbonyl group.

Recognize that conjugate addition (1,4-addition) involves the addition of a nucleophile to the beta position of an alpha, beta-unsaturated carbonyl compound.

Select an appropriate alpha, beta-unsaturated carbonyl compound as the starting material. In this case, cyclohexenone can be used as it has the necessary unsaturation for conjugate addition.

Choose a suitable cuprate reagent for the conjugate addition. A common choice is a lithium diorganocuprate, such as lithium cyclopropylcuprate (LiCu(C3H5)2), which can deliver the cyclopropyl group to the beta position.

Outline the reaction: The lithium cyclopropylcuprate will add to the beta position of cyclohexenone, resulting in the formation of the desired cyclohexanone derivative with a cyclopropyl group at the beta position.

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Key Concepts

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

Conjugate Addition

Conjugate addition refers to the nucleophilic addition of a reagent to the β-carbon of an α,β-unsaturated carbonyl compound. This reaction typically involves the addition of a nucleophile to the double bond, resulting in the formation of a new carbon-carbon bond. Understanding this mechanism is crucial for predicting the products of reactions involving cuprates and unsaturated carbonyls.

Cuprates

Cuprates are organocopper reagents, commonly represented as R2CuLi, where R is an organic group. They are powerful nucleophiles used in organic synthesis, particularly for conjugate additions to α,β-unsaturated carbonyl compounds. Their ability to selectively add to the β-position makes them valuable for forming complex molecules in a controlled manner.

Reagent and Reactant Selection

Choosing the appropriate reagent and reactant is essential for successful conjugate addition. The reactant is typically an α,β-unsaturated carbonyl compound, while the reagent is a cuprate that can provide the necessary nucleophile. Understanding the structure and reactivity of both components helps in predicting the outcome of the reaction and the formation of desired products.

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Related Practice

Textbook Question

Predict the product of the following reactions.

(b)

Textbook Question

Predict the product of the following reactions.

(c)

Textbook Question

a. Propose a mechanism for the following reaction:

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.

(a)

Textbook Question

What is the major product of each of the following reactions?

Textbook Question

Propose a mechanism for the conjugate addition of a nucleophile (Nuc:^–) to acrylonitrile (H₂C=CHCN). Use resonance forms to show how the cyano activate the double bond toward conjugate addition.

Textbook Question

Propose a mechanism for the conjugate addition of a nucleophile (Nuc:^–) to acrylonitrile (H₂C=CHCN) and to nitroethylene. Use resonance forms to show how the cyano and nitro groups activate the double bond toward conjugate addition.

Multiple Choice

Predict the major, organic product for the following reaction.

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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.(b)

Key Concepts

Conjugate Addition

Cuprates

Reagent and Reactant Selection

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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.
(b)