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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6:05 minutes

Problem 46a

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)

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Identify the target molecule as an ester with a conjugated system, specifically a β-keto ester.

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

Determine the structure of the α,β-unsaturated carbonyl compound needed. In this case, it would be an α,β-unsaturated ester with the same carbon skeleton minus the group added by the cuprate.

Select a suitable cuprate reagent. Cuprates are organocopper compounds, typically of the form R2CuLi, where R is an alkyl or aryl group. Choose a cuprate that will add the desired alkyl group to the β-position.

Combine the α,β-unsaturated ester with the chosen cuprate reagent under appropriate conditions to achieve the conjugate addition, forming the target molecule.

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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 an α,β-unsaturated carbonyl compound. This reaction typically involves the addition of a nucleophile to the β-carbon of 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 systems.

Cuprates

Cuprates are organometallic compounds containing copper, often used as nucleophiles in organic synthesis. They are typically derived from lithium diorganocopper reagents, which can effectively add to electrophilic centers in conjugate addition reactions. Recognizing the reactivity and selectivity of cuprates is essential for designing reactions that yield specific products.

Electrophiles

Electrophiles are species that accept electron pairs from nucleophiles during chemical reactions. In the context of conjugate addition, the α,β-unsaturated carbonyl compounds act as electrophiles, where the carbonyl carbon is particularly susceptible to nucleophilic attack. Identifying suitable electrophiles is key to successfully predicting and executing conjugate addition reactions.

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Related Practice

Textbook Question

Predict the product of the following reactions.

(a)

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.

(b)

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.

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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.(a)

Key Concepts

Conjugate Addition

Cuprates

Electrophiles

Watch next

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)