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 43b
Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 43bCapitolo 22, Problema 43b
Predict the products of the following electrophilic aromatic substitution reactions.
(b) 
Guida verificata passo dopo passo1
Identify the type of reaction: The reaction shown is an electrophilic aromatic substitution (EAS) where a sulfonation reaction is taking place. The reagents SO3 and H2SO4 are used to introduce a sulfonic acid group (SO3H) onto the aromatic ring.
Determine the directing effects of substituents: The acyl group (C=O) attached to the benzene ring is a meta-directing group due to its electron-withdrawing nature. This means that the incoming electrophile (SO3) will preferentially add to the meta position relative to the acyl group.
Draw the intermediate: The electrophile, SO3, will attack the benzene ring at the meta position, forming a sigma complex (arenium ion) where the positive charge is delocalized over the ring.
Reform the aromatic system: The loss of a proton from the sigma complex will restore the aromaticity of the benzene ring, resulting in the formation of the sulfonated product.
Predict the final product: The final product will be a benzene ring with a sulfonic acid group (SO3H) at the meta position relative to the acyl group, due to the directing effects of the acyl substituent.
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Concetti chiave
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Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a reaction where an aromatic ring, such as benzene, undergoes substitution of one of its hydrogen atoms by an electrophile. This process involves the formation of a highly reactive intermediate called an arenium ion, which is stabilized by resonance. The reaction typically proceeds through two main steps: the formation of the arenium ion and the subsequent deprotonation to restore aromaticity.
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03:07
EAS Review
Sulfonation Reaction
Sulfonation is a type of electrophilic aromatic substitution where sulfur trioxide (SO3) acts as the electrophile, often in the presence of sulfuric acid (H2SO4) to form the sulfonic acid group (-SO3H) on the aromatic ring. This reaction is reversible and is used to introduce sulfonic acid groups into aromatic compounds, which can influence the compound's solubility and reactivity.
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04:33Forcing Ortho substitution
Directing Effects of Substituents
In EAS reactions, substituents already present on the aromatic ring can influence the position where new groups are added. Electron-withdrawing groups, like the carbonyl group in an acyl group, typically direct incoming electrophiles to the meta position relative to themselves. This is due to their ability to stabilize the arenium ion intermediate through resonance and inductive effects, affecting the regioselectivity of the reaction.
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Percorso guidato
2:02Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Concept 1
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