Textbook Question
Predict the products of the following nucleophilic aromatic substitution reactions.
(c)
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Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- 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 I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: 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 I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: 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: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 23 - Benzene I: Aromatic Stability and Substitution ReactionsProblem 43b
Mullins 1st EditionCh. 23 - Benzene I: Aromatic Stability and Substitution ReactionsProblem 43bChapter 22, Problem 43b
Predict the products of the following electrophilic aromatic substitution reactions.
(b) 
Verified step by step guidance1
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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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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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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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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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Related Practice
Textbook Question
Beginning with benzene, synthesize the following substituted benzenes. The ideal number of steps is indicated.
(d)
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Textbook Question
Predict the major product of the following electrophilic aromatic substitution reactions.
(c)
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Textbook Question
Predict the major product of the following electrophilic aromatic substitution reactions.
(b)
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Textbook Question
With a small electron-donating group on the ring, it is possible to get as much as a 2:1 ratio of ortho to para. Why might this be?
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Textbook Question
In Section 23.7.4, we learned that Friedel–Crafts alkylation suffers from overalkylation.
(a) Draw the product of a Friedel–Crafts reaction that resulted in three methyl groups adding to the ring.
(b) Why is hard to stop at the addition of one alkyl group?
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