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?
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Ch. 21 - Conjugated Systems I: Stability and Addition Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 21 - Conjugated Systems I: Stability and Addition ReactionsProblem 46b
Mullins 1st EditionCh. 21 - Conjugated Systems I: Stability and Addition ReactionsProblem 46bChapter 20, Problem 46b
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.
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1,2 vs 1,4 Addition
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
Would you expect the following molecules to absorb in the UV–visible region of the electromagnetic spectrum?
(a)
(b)
(c)
(d)
(e)
1
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Textbook Question
Predict the product of the following reactions.
(c)
1
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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)
2
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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)
1
views
Textbook Question
Predict the product of the following reactions.
(b)
2
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