Textbook Question
Predict the major products of the following reactions.
(a) 2,4-dinitrochlorobenzene + NaOCH3
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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 53c
Predict the major products of the following reactions.
(c) nitrobenzene + fuming sulfuric acid
Verified step by step guidance1
Step 1: Analyze the reactants. Nitrobenzene (C6H5NO2) is an aromatic compound with a nitro group (-NO2) attached to the benzene ring. Fuming sulfuric acid is a mixture of sulfuric acid (H2SO4) and sulfur trioxide (SO3), which is used for sulfonation reactions.
Step 2: Understand the reaction mechanism. Sulfonation of aromatic compounds involves the electrophilic substitution of a hydrogen atom on the benzene ring with a sulfonic acid group (-SO3H). The nitro group (-NO2) is an electron-withdrawing group, which deactivates the benzene ring and directs incoming electrophiles to the meta position relative to itself.
Step 3: Predict the major product. Since the nitro group is meta-directing, the sulfonic acid group (-SO3H) will be introduced at the meta position relative to the nitro group on the benzene ring.
Step 4: Compare the provided options. Among the given structures (A, B, C, D), identify the one where the sulfonic acid group (-SO3H) is at the meta position relative to the nitro group (-NO2).
Step 5: Confirm the correct structure. Based on the sulfonation mechanism and the directing effects of the nitro group, the major product will be the structure where the -SO3H group is meta to the -NO2 group. This corresponds to option C in the provided image.
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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 fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this process, the aromaticity of the ring is preserved, and the reaction typically involves the formation of a sigma complex. Understanding EAS is crucial for predicting the products of reactions involving aromatic compounds, such as nitrobenzene with fuming sulfuric acid.
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EAS Review
Activating and Deactivating Groups
In EAS reactions, substituents on the aromatic ring can either activate or deactivate the ring towards further substitution. Activating groups, such as -OH or -NH2, increase the electron density of the ring, making it more reactive, while deactivating groups, like -NO2 or -SO3H, withdraw electron density and make the ring less reactive. Recognizing the nature of substituents is essential for predicting the major products of the reaction.
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Ortho/Para vs. Meta Directing Effects
The position at which a new substituent is added to an aromatic ring during EAS is influenced by the existing substituents. Ortho and para directing groups favor substitution at the 2 or 4 positions relative to themselves, while meta directing groups favor substitution at the 3 position. This concept is vital for determining the specific products formed when nitrobenzene reacts with fuming sulfuric acid, as the existing nitro group will influence the site of new substitution.
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Related Practice
Textbook Question
Predict the major products of the following reactions.
(d) nitrobenzene + acetyl chloride + AlCl3
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Textbook Question
Predict the major products of the following reactions.
(e) p-methylanisole + acetyl chloride + AlCl3
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Textbook Question
Predict the major products of the following reactions.
(b) phenol + tert-butyl chloride + AlCl3
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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 of the following reactions.
(f) p-methylanisole + Br2 , light
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