Textbook Question
Predict the products of the following nucleophilic aromatic substitution reactions.
(c)
1005
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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 45c
Mullins 1st EditionCh. 23 - Benzene I: Aromatic Stability and Substitution ReactionsProblem 45cChapter 22, Problem 45c
Predict the major product of the following electrophilic aromatic substitution reactions.
(c) 
Verified step by step guidance1
Identify the type of reaction: The reaction shown is an electrophilic aromatic substitution (EAS), where a nitro group (NO2) will be introduced to the aromatic ring.
Determine the directing effects of substituents: The benzene ring has a chlorine (Cl) substituent, which is an ortho/para-directing group due to its electron-withdrawing nature through resonance, and a carbonyl group (C=O) which is a meta-directing group due to its electron-withdrawing nature through induction.
Consider the reaction conditions: The presence of HNO3 and H2SO4 indicates a nitration reaction, where the nitronium ion (NO2+) is the electrophile.
Predict the major product: Given the presence of both ortho/para and meta-directing groups, the position of the nitro group will be influenced by the stronger directing effect. The chlorine group, being ortho/para-directing, will favor substitution at the ortho or para position relative to itself.
Select the most likely position: The para position relative to the chlorine is less sterically hindered compared to the ortho position, making it the most favorable site for nitration. Therefore, the major product will have the nitro group at the para position relative to the chlorine 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 a hydrogen atom 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 requires a strong acid to generate the electrophile, as seen with the use of HNO3 and H2SO4 to produce the nitronium ion (NO2+).
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Directing Effects of Substituents
Substituents on an aromatic ring influence the position where new groups are added during EAS. Electron-donating groups (EDGs) generally direct new substituents to the ortho and para positions, while electron-withdrawing groups (EWGs) direct them to the meta position. In the given structure, the chlorine atom is an ortho/para director due to its lone pairs, while the carbonyl group is a meta director due to its electron-withdrawing nature.
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Reactivity and Orientation in EAS
The reactivity and orientation in EAS are influenced by the nature of substituents on the aromatic ring. In the given molecule, the presence of both a chlorine atom and a carbonyl group creates competing directing effects. Chlorine, being a weak electron-donating group, directs ortho/para, while the carbonyl group, a strong electron-withdrawing group, directs meta. The major product is often determined by the stronger directing influence, which in this case is the meta-directing carbonyl group.
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Related Practice
Textbook Question
Beginning with benzene, synthesize the following substituted benzenes. The ideal number of steps is indicated.
(d)
1168
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Textbook Question
Predict the major product of the following electrophilic aromatic substitution reactions.
(b)
1161
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Textbook Question
Assume that Ha is the proton removed in the first step of the benzyne mechanism with p-chlorotoluene. Draw the benzyne intermediate and identify the two products that will result.
360
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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?
563
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Textbook Question
Predict the products of the following electrophilic aromatic substitution reactions.
(b)
545
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