Textbook Question
Predict the product(s) of the following nucleophilic aromatic substitution reactions occurring by the benzyne mechanism.
(b)
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Ch. 23 - Benzene I: Aromatic Stability and Substitution 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. 23 - Benzene I: Aromatic Stability and Substitution ReactionsProblem 59a
Mullins 1st EditionCh. 23 - Benzene I: Aromatic Stability and Substitution ReactionsProblem 59aChapter 22, Problem 59a
Predict the products of the following reactions.
(a) 
Verified step by step guidance1
Identify the type of reaction: The reaction involves a bromopyridine and a stannane derivative in the presence of a palladium catalyst, indicating a Stille coupling reaction.
Understand the Stille coupling mechanism: This reaction involves the coupling of an organostannane with an organohalide, facilitated by a palladium catalyst, to form a new carbon-carbon bond.
Determine the coupling partners: In this reaction, the pyridine ring with the bromine atom is the organohalide, and the furan ring with the tin group is the organostannane.
Predict the product: The new carbon-carbon bond will form between the carbon atom of the pyridine ring that was bonded to the bromine and the carbon atom of the furan ring that was bonded to the tin group.
Consider the stereochemistry and regiochemistry: Since the reaction involves aromatic rings, the product will likely retain the aromaticity and the substitution pattern of the original reactants.
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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 reaction between an organotin compound and an organic halide or pseudohalide. It is used to form carbon-carbon bonds, often between aromatic rings. In this reaction, the organotin compound (SnBu3) reacts with the brominated aniline in the presence of a palladium catalyst to form a new C-C bond, resulting in the coupling of the two aromatic systems.
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Stille Reaction
Role of Palladium Catalyst
Palladium catalysts, such as Pd(PPh3)4, are crucial in facilitating cross-coupling reactions like the Stille reaction. They work by forming a complex with the organic halide, which undergoes oxidative addition to the palladium center. This step is followed by transmetalation with the organotin compound and reductive elimination to form the desired C-C bond, regenerating the palladium catalyst for further reaction cycles.
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Organotin Compounds
Organotin compounds, such as the stannylated furan shown in the reaction, are key reagents in Stille coupling reactions. They contain a tin atom bonded to carbon groups, which can transfer an organic group to a palladium complex during the transmetalation step. This transfer is essential for forming the new carbon-carbon bond in the final product, making organotin compounds valuable in synthetic organic chemistry.
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Related Practice
Textbook Question
(i) Classify the following molecules as aromatic, nonaromatic, or antiaromatic.
(ii) For aromatic molecules, solve for n in Hückel’s rule. For all other molecules, explain which rule of aromaticity is being broken.
(a)
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Textbook Question
Suggest two coupling partners that could be used to synthesize the compounds shown making the indicated C―C bonds.
(a)
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Textbook Question
Predict the products of the following reactions.
(a)
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Textbook Question
Conversion of t-butylbenzene to a phenol results in two products when the reaction occurs through the benzyne mechanism. Devise a sequence involving a diazonium ion in which only one phenol product is produced.
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Textbook Question
Predict the products of the following reactions.
(b)
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