Textbook Question
Based on the stereochemical result alone, how can you tell that this reaction does not proceed by an Sₙ2 mechanism?
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Ch. 16 - Metals in Organic Chemistry
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
Chapter 15, Problem 33a
Predict the product of the diorganocuprate cross-coupling reactions shown.
(a) 
Verified step by step guidance1
Identify the reactants involved in the diorganocuprate cross-coupling reaction. Typically, these reactions involve an organocuprate reagent (R2CuLi) and an organic halide (R'-X).
Understand the role of the organocuprate reagent. In this reaction, the organocuprate acts as a nucleophile, where one of the organic groups (R) will be transferred to the organic halide.
Determine the leaving group in the organic halide. The halide (X) is the leaving group, which will be replaced by the organic group from the organocuprate.
Predict the product by coupling the organic group from the organocuprate with the organic group from the halide. The new bond formed will be between the carbon of the organocuprate and the carbon of the organic halide.
Consider any stereochemical or regiochemical outcomes. If the organic halide is chiral or has multiple reactive sites, consider how the reaction conditions might affect the stereochemistry or regioselectivity of the product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Diorganocuprate Reagents
Diorganocuprate reagents, also known as Gilman reagents, are organocopper compounds typically represented as R2CuLi. They are used in organic synthesis for forming carbon-carbon bonds through nucleophilic substitution reactions. These reagents are particularly useful for coupling with alkyl, aryl, or vinyl halides to form new carbon-carbon bonds, often with high selectivity and mild reaction conditions.
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Reagents
Cross-Coupling Reactions
Cross-coupling reactions are a class of reactions where two different organic groups are joined together with the aid of a metal catalyst. In the context of diorganocuprate reagents, these reactions involve the coupling of an organocuprate with an organic halide to form a new carbon-carbon bond. The reaction typically proceeds through a mechanism involving oxidative addition, transmetalation, and reductive elimination, resulting in the formation of the desired coupled product.
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Reaction Mechanism
Understanding the mechanism of diorganocuprate cross-coupling is crucial for predicting the reaction product. The mechanism generally involves the oxidative addition of the organic halide to the copper center, followed by transmetalation where the organic group from the cuprate is transferred to the metal center. Finally, reductive elimination occurs, forming the new carbon-carbon bond and regenerating the copper catalyst. This sequence ensures the selective formation of the desired product.
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Related Practice
Textbook Question
Predict the product of the diorganocuprate cross-coupling reactions shown.
(b)
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Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(b)
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Textbook Question
The trimethylsilyl (TMS) group, used as a protecting group for alcohols, can also be used a protecting group for terminal alkynes. Show how TMS-acetylene could be used to link together two aryl halides using the Sonogashira reaction. [Hint: Deprotection of the TMS-acetylene can be done using KF in H₂O.]
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Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(a)
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Textbook Question
Predict the product of the diorganocuprate cross-coupling reactions shown.
(c)
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