Textbook Question
Predict the product of the following Stille coupling reactions.
(b)
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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 24a
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) 
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Identify the bond indicated by the blue arrow. This bond is between the cyclohexene ring and the pyridine ring.
To work backward, consider the retrosynthetic analysis. Break the bond at the blue arrow to form two fragments: one containing the cyclohexene ring and the other containing the pyridine ring.
For the cyclohexene fragment, consider it as an organozinc halide. This means replacing the bond with a zinc halide group, such as ZnBr.
For the pyridine fragment, consider it as an organohalide. This means replacing the bond with a halogen, such as Br.
Alternatively, reverse the roles: consider the pyridine fragment as the organozinc halide and the cyclohexene fragment as the organohalide. This provides the second possibility for the synthesis.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Organozinc Reagents
Organozinc reagents, such as RZnX, are organometallic compounds where a carbon atom is bonded to zinc. They are highly reactive and can act as nucleophiles in organic reactions, particularly in coupling reactions. Understanding their reactivity and how they can form carbon-carbon bonds is essential for synthesizing complex organic molecules.
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01:52
Reagents
Organohalides
Organohalides are organic compounds containing at least one halogen atom (F, Cl, Br, I) bonded to a carbon atom. They serve as important intermediates in organic synthesis, often undergoing nucleophilic substitution or elimination reactions. Recognizing the structure and reactivity of organohalides is crucial for designing synthetic pathways.
Nucleophilic Substitution Reactions
Nucleophilic substitution reactions involve the replacement of a leaving group (such as a halide) by a nucleophile. These reactions can proceed via two main mechanisms: SN1 (unimolecular) and SN2 (bimolecular). Understanding these mechanisms helps predict the outcome of reactions involving organohalides and organozinc reagents, which is key to constructing the desired molecular structures.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Related Practice
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
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Textbook Question
Predict the product of the following Negishi coupling reactions.
(b)
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Textbook Question
Predict the product of the following Stille coupling reactions.
(a)
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Textbook Question
To determine the stereochemistry of curacin A by synthesis, it would have been necessary to prepare all stereoisomers of the C₁₇―C₂₀ cyclopropane fragment. How would the reaction in Figure 16.30 be modified to produce the other stereoisomers shown here?
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Textbook Question
Predict the product of the following Negishi coupling reactions.
(a)
1107
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