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 24b
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) 
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Identify the bond indicated by the blue arrow. This bond is between the cyclopentyl group and the oxygen atom in the ether linkage.
To work backward, consider breaking the molecule at the indicated bond to form two fragments: a cyclopentyl group and an ether group.
The cyclopentyl group can be derived from a cyclopentyl organozinc halide. Consider the structure of cyclopentyl zinc bromide (C5H9ZnBr) as a potential organozinc halide.
The ether group can be derived from an organohalide. Consider the structure of 2-bromoethoxybenzene (C8H9BrO) as a potential organohalide.
Propose a reaction where the cyclopentyl zinc bromide reacts with 2-bromoethoxybenzene to form the desired ether linkage, using a coupling reaction such as the Negishi coupling.
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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, typically represented as RZnX, are organometallic compounds where a zinc atom is bonded to an organic group (R) and a halide (X). They are highly reactive and serve as nucleophiles in organic synthesis, allowing for the formation of carbon-carbon bonds through reactions with electrophiles. Understanding their reactivity and how they can be synthesized from organohalides is crucial for constructing complex organic molecules.
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01:52
Reagents
Organohalides
Organohalides, or haloalkanes, are organic compounds containing at least one halogen atom (F, Cl, Br, I) bonded to a carbon atom. They are important intermediates in organic synthesis, as they can undergo various reactions, including nucleophilic substitution and elimination. Recognizing the structure and reactivity of organohalides is essential for determining how to create the desired organozinc halide for bond formation.
Nucleophilic Substitution Reactions
Nucleophilic substitution reactions involve the replacement of a leaving group (often a halide) in a molecule with a nucleophile. These reactions can occur via two main mechanisms: SN1 (unimolecular) and SN2 (bimolecular), each with distinct kinetics and stereochemical outcomes. Understanding these mechanisms is vital for predicting the products of reactions involving organozinc and organohalide compounds, especially when constructing new carbon-carbon bonds.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Related Practice
Textbook Question
Predict the product of the following Negishi coupling reactions.
(b)
941
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Textbook Question
Predict the product of the following Stille coupling reactions.
(a)
997
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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
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Textbook Question
Predict the product of the following Sonogashira coupling reactions.
(a)
1006
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Textbook Question
Predict the product of the following Negishi coupling reactions.
(a)
1107
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