Textbook Question
Predict the major products of the following reactions.
(d) nitrobenzene + acetyl chloride + AlCl3
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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 53a
Predict the major products of the following reactions.
(a) 2,4-dinitrochlorobenzene + NaOCH3
Verified step by step guidance1
Step 1: Analyze the reactants. The starting material is 2,4-dinitrochlorobenzene, which contains two electron-withdrawing nitro groups (-NO2) at the 2 and 4 positions and a chlorine atom (-Cl) at the 1 position. The reagent is sodium methoxide (NaOCH3), a strong nucleophile and base.
Step 2: Understand the reaction mechanism. This reaction proceeds via nucleophilic aromatic substitution (SNAr). The electron-withdrawing nitro groups activate the aromatic ring by stabilizing the negative charge formed during the intermediate step, making the chlorine atom susceptible to nucleophilic attack.
Step 3: Predict the site of substitution. The chlorine atom is the leaving group, and the methoxide ion (CH3O-) will replace it. The nitro groups at the 2 and 4 positions enhance the reactivity of the ring by withdrawing electron density, facilitating the substitution reaction.
Step 4: Draw the product structure. After substitution, the chlorine atom is replaced by the methoxy group (-OCH3), resulting in 2,4-dinitroanisole. The nitro groups remain intact at the 2 and 4 positions, and the methoxy group is attached to the 1 position.
Step 5: Verify the major product. The major product is 2,4-dinitroanisole, as the reaction is regioselective due to the activating effect of the nitro groups. This matches the expected outcome of the nucleophilic aromatic substitution mechanism.
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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. The reaction typically involves the formation of a sigma complex, where the aromaticity is temporarily lost, followed by deprotonation to restore aromaticity. Understanding the nature of the electrophile and the substituents on the aromatic ring is crucial for predicting the major products.
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Activating and Deactivating Groups
Substituents on an aromatic ring can either activate or deactivate the ring towards electrophilic substitution. Activating groups, such as -OCH3, increase the electron density of the ring, making it more reactive, while deactivating groups, like -NO2, withdraw electron density and make the ring less reactive. The position of these groups (ortho, meta, para) also influences the regioselectivity of the substitution reaction.
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Regioselectivity in EAS Reactions
Regioselectivity refers to the preference of an electrophilic substitution reaction to occur at a specific position on the aromatic ring. The presence of substituents can direct incoming electrophiles to ortho, meta, or para positions based on their electronic effects. For example, activating groups typically direct substitution to the ortho and para positions, while deactivating groups often direct it to the meta position.
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Related Practice
Textbook Question
Predict the major products of the following reactions.
(c) nitrobenzene + fuming sulfuric acid
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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.
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
(l) CH2(COCl)2, AlCl3
634
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Textbook Question
Predict the major products of the following reactions.
(b) phenol + tert-butyl chloride + AlCl3
1822
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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
1612
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