Textbook Question
Predict the major products formed when benzene reacts (just once) with the following reagents.
(i) iodine + HNO3
Ch. 17 - Reactions of Aromatic Compounds
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 17, Problem 50j
Predict the major products formed when benzene reacts (just once) with the following reagents.
(j) nitric acid + sulfuric acid
Verified step by step guidance1
Step 1: Recognize the type of reaction. The reaction of benzene with nitric acid (HNO₃) in the presence of sulfuric acid (H₂SO₄) is an electrophilic aromatic substitution reaction, specifically nitration.
Step 2: Understand the role of the reagents. Sulfuric acid acts as a catalyst and protonates nitric acid, generating the nitronium ion (NO₂⁺), which is the electrophile in this reaction. The reaction can be represented as: .
Step 3: Identify the electrophile and its interaction with benzene. The nitronium ion (NO₂⁺) attacks the π-electron cloud of benzene, forming a resonance-stabilized carbocation intermediate (arenium ion).
Step 4: Regenerate aromaticity. A proton (H⁺) is removed from the carbocation intermediate by the conjugate base (HSO₄⁻), restoring the aromaticity of the benzene ring and forming nitrobenzene as the major product.
Step 5: Summarize the major product. The major product of this reaction is nitrobenzene (), where a nitro group (-NO₂) is substituted onto the benzene ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for understanding how benzene and its derivatives react, as the stability of the aromatic system allows for selective substitution rather than addition.
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Nitration of Benzene
Nitration is a specific type of electrophilic aromatic substitution where a nitro group (NO2) is introduced into the benzene ring. This reaction typically involves the use of a nitrating mixture, such as nitric acid and sulfuric acid, which generates the nitronium ion (NO2+), the active electrophile that attacks the aromatic ring.
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Regioselectivity in Electrophilic Aromatic Substitution
Regioselectivity refers to the preference of an electrophilic substitution reaction to occur at specific positions on the aromatic ring. In the case of nitration of benzene, the nitro group can be introduced at different positions, but due to the stability of the intermediates formed, the major product is typically the nitrobenzene, with the nitro group being added to the ortho or para positions relative to the original hydrogen.
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Related Practice
Textbook Question
Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.
a. 1-phenyl-1-bromobutane
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Textbook Question
Predict the major products formed when benzene reacts (just once) with the following reagents.
(k) carbon monoxide, HCl, and AlCl3/CuCl
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Textbook Question
Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.
b. 1-phenyl-1-methoxybutane
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Textbook Question
Predict the major products formed when benzene reacts (just once) with the following reagents.
(h) benzoyl chloride + AlCl3
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Textbook Question
Predict the major products formed when benzene reacts (just once) with the following reagents.
(g) 1-chloro-2,2-dimethylpropane + AlCl3
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