Textbook Question
Work backward to an appropriate organozinc halide and organohalide to make the bonds indicated by the blue arrows. There may be two possibilities for each.
(b)
547
views
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 25b
Predict the product of the following Stille coupling reactions.
(b) 
Verified step by step guidance1
Identify the reactants involved in the Stille coupling reaction. The first reactant is a lithium-substituted aromatic compound, and the second reactant is a pyridine derivative with bromine and fluorine substituents.
Understand the role of each reagent in the reaction. Bu3SnCl is used to convert the lithium-substituted aromatic compound into a stannane, which is necessary for the Stille coupling. Pd(PPh3)4 is the palladium catalyst that facilitates the coupling reaction between the stannane and the bromine-substituted pyridine.
Convert the lithium-substituted aromatic compound into a stannane by reacting it with Bu3SnCl. This step involves the formation of a carbon-tin bond, replacing the lithium atom with a tributyltin group.
Recognize the mechanism of the Stille coupling reaction. The palladium catalyst will facilitate the transmetalation step, where the stannane transfers its organic group to the palladium, forming a palladium-organic complex.
Predict the final product of the reaction. The organic group from the stannane will couple with the pyridine derivative at the position where the bromine was located, resulting in the formation of a new carbon-carbon bond between the aromatic ring and the pyridine ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stille Coupling Reaction
The Stille coupling reaction is a palladium-catalyzed cross-coupling process that forms carbon-carbon bonds between organotin compounds and organic halides or pseudohalides. It is widely used in organic synthesis due to its ability to form complex molecules with high selectivity and functional group tolerance. The reaction typically involves a tin reagent, a halide, and a palladium catalyst.
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03:20
Stille Reaction
Organotin Reagents
Organotin reagents, such as Bu3SnCl, are key components in Stille coupling reactions. These reagents contain a tin atom bonded to organic groups, which can transfer an organic moiety to a palladium catalyst. The organotin compound in the reaction serves as a nucleophile, facilitating the formation of a new carbon-carbon bond with the organic halide or pseudohalide.
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01:52Reagents
Palladium Catalysis
Palladium catalysis is crucial in Stille coupling reactions, where palladium complexes, like Pd(PPh3)4, facilitate the formation of carbon-carbon bonds. The palladium catalyst undergoes oxidative addition with the organic halide, transmetalation with the organotin reagent, and reductive elimination to form the coupled product. This catalytic cycle is essential for the efficiency and selectivity of the reaction.
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Related Practice
Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(b)
890
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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.]
1019
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Textbook Question
Predict the product of the following Stille coupling reactions.
(a)
997
views
Textbook Question
Work backward to an appropriate organozinc halide and organohalide to make the bonds indicated by the blue arrows. There may be two possibilities for each.
(a)
855
views
Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(a)
1006
views