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 58
Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 58Capitolo 22, Problema 58
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.
Guida verificata passo dopo passo1
Begin by converting t-butylbenzene to a diazonium salt. First, perform a nitration reaction by treating t-butylbenzene with concentrated HNO3 and H2SO4 to introduce a nitro group on the benzene ring.
Reduce the nitro group to an amino group using a reducing agent such as Sn/HCl or Fe/HCl, resulting in t-butylaniline.
Convert the amino group to a diazonium ion by treating t-butylaniline with NaNO2 and HCl at 0-5°C. This forms the diazonium salt, t-butylbenzenediazonium chloride.
Perform a Sandmeyer reaction by treating the diazonium salt with Cu2O in water, which will replace the diazonium group with a hydroxyl group, forming the desired phenol product.
This sequence ensures that only one phenol product is formed, avoiding the formation of multiple isomers as seen in the benzyne mechanism.
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Benzyne Mechanism
The benzyne mechanism is a reaction pathway involving the formation of a highly reactive intermediate known as benzyne. This intermediate is generated by the elimination of a leaving group from a benzene derivative, leading to a triple bond between two carbon atoms in the aromatic ring. The reactivity of benzyne allows for various nucleophilic attacks, which can result in multiple products, complicating the synthesis of a single desired product.
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General Mechanism
Diazonium Ion
Diazonium ions are highly reactive intermediates formed from primary aromatic amines and nitrous acid. They are characterized by the presence of a positively charged nitrogen atom bonded to a benzene ring. In organic synthesis, diazonium ions can undergo various transformations, including coupling reactions, which can be strategically used to introduce functional groups like hydroxyl groups, leading to the formation of phenols in a controlled manner.
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Percorso guidato
3:39Metal Ion Catalysis Concept 1
Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process typically involves the generation of a sigma complex, followed by deprotonation to restore aromaticity. In the context of converting t-butylbenzene to phenol, EAS can be utilized to introduce functional groups selectively, allowing for the synthesis of a single phenol product when combined with subsequent reactions involving diazonium ions.
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03:07EAS Review
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