Domanda del libro di testo
Predict the product(s) of the following nucleophilic aromatic substitution reactions occurring by the benzyne mechanism.
(b)
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Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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TOC.tableOfContents
- 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 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: 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 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: 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: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 59a
Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 59aCapitolo 22, Problema 59a
Predict the products of the following reactions.
(a) 
Guida verificata passo dopo passo1
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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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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03:20
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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Percorso guidato
3:21Catalytic Allylic Alkylation Concept 1
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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01:40Defining meso compounds.
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(i) Classify the following molecules as aromatic, nonaromatic, or antiaromatic.
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Predict the products of the following reactions.
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Predict the products of the following reactions.
(b)
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