Domanda del libro di testo
Predict the products of the following nucleophilic aromatic substitution reactions.
(c)
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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 56b
Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 56bCapitolo 22, Problema 56b
Predict the product(s) of the following nucleophilic aromatic substitution reactions occurring by the benzyne mechanism.
(b) 
Guida verificata passo dopo passo1
Identify the substrate and the nucleophile: The substrate is a bromobenzene derivative with a methyl group ortho to the bromine. The nucleophile is methoxide ion (CH₃O⁻) in methanol.
Recognize the reaction conditions: The reaction is carried out at 100°C, which is conducive to the benzyne mechanism, a type of nucleophilic aromatic substitution.
Understand the benzyne mechanism: This mechanism involves the elimination of the leaving group (Br) to form a highly reactive benzyne intermediate. This occurs through the removal of a proton adjacent to the leaving group, forming a triple bond in the benzene ring.
Predict the formation of the benzyne intermediate: The base (NaOCH₃) abstracts a proton from the carbon adjacent to the bromine, resulting in the elimination of bromide ion and formation of the benzyne intermediate.
Determine the product formation: The methoxide ion can attack either carbon of the benzyne intermediate, leading to a mixture of products. The nucleophile adds to the benzyne, restoring aromaticity and forming a methoxy-substituted benzene.
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Concetti chiave
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Nucleophilic Aromatic Substitution (NAS)
Nucleophilic aromatic substitution is a reaction where a nucleophile replaces a leaving group on an aromatic ring. This process typically occurs when the aromatic compound has electron-withdrawing groups that stabilize the negative charge developed during the reaction. The mechanism can proceed via different pathways, including the benzyne mechanism, which involves the formation of a highly reactive intermediate known as benzyne.
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02:10
NAS in the addition-elimination pathway
Benzyne Mechanism
The benzyne mechanism is a specific pathway for nucleophilic aromatic substitution that involves the formation of a benzyne intermediate. This occurs when a leaving group, such as bromine, is eliminated to create a triple bond between two carbon atoms in the aromatic ring. The nucleophile then attacks this highly reactive intermediate, leading to the substitution product. This mechanism is particularly relevant when the aromatic compound lacks strong electron-withdrawing groups.
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06:06General Mechanism
Role of Sodium Methoxide and Methanol
Sodium methoxide (NaOCH3) acts as a strong nucleophile in the reaction, while methanol (CH3OH) serves as the solvent. The nucleophile attacks the benzyne intermediate formed during the reaction, facilitating the substitution process. The choice of methanol as a solvent is important as it can stabilize the reaction intermediates and help in the solvation of the nucleophile, enhancing the overall reaction efficiency.
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03:19Sodium Alkynide Alkylation
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