Domanda del libro di testo
Beginning with benzene, synthesize the following substituted benzenes. The ideal number of steps is indicated.
(d)
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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 40b
Mullins 1st EditionCh. 23 - Benzene 1: Aromatic Stability and Substitution ReactionsProblema 40bCapitolo 22, Problema 40b
Predict the major product 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 electrophile in this reaction is the sulfur trioxide (SO₃) in the presence of sulfuric acid (H₂SO₄).
Determine the directing effects of the substituent: The substituent on the benzene ring is a thioether group (S-CH₃). This group is an ortho/para director due to the lone pair of electrons on the sulfur atom, which can donate electron density into the benzene ring through resonance.
Predict the position of substitution: Since the thioether group is an ortho/para director, the incoming electrophile (SO₃) will preferentially attack the ortho and para positions relative to the sulfur atom on the benzene ring.
Consider steric and electronic factors: The para position is often favored over the ortho position due to less steric hindrance, making it the more likely site for substitution.
Draw the major product: The major product will be the para-substituted sulfonic acid derivative, where the SO₃H group is added to the para position relative to the thioether group on the benzene ring.
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Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. The reaction involves the formation of a highly reactive carbocation intermediate, known as the sigma complex, which is stabilized by resonance. The final step is the deprotonation to restore aromaticity, resulting in the substitution of the electrophile onto the ring.
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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, typically in the presence of sulfuric acid (H2SO4). This reaction introduces a sulfonic acid group (SO3H) onto the aromatic ring. The process is reversible, and the position of substitution is influenced by existing substituents on the ring, which can direct the incoming group to ortho, meta, or para positions.
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04:33Forcing Ortho substitution
Directing Effects of Substituents
Substituents on an aromatic ring can influence the position of incoming electrophiles during EAS reactions. Electron-donating groups, like alkyl or methoxy groups, typically direct electrophiles to ortho and para positions, while electron-withdrawing groups, such as nitro or carbonyl groups, direct them to the meta position. The sulfur substituent in the given structure is an electron-donating group, which will direct the sulfonation to the ortho and para positions.
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Percorso guidato
2:02Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Concept 1
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(b) Why is hard to stop at the addition of one alkyl group?
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