Textbook Question
What products would you expect from the following coupling reactions?
(c)
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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 57a,b
Give the structures of compounds A through B in the following series of reactions.
Verified step by step guidance1
Step 1: Analyze the first reaction. The starting material is benzene, and it reacts with an acyl chloride (CH3CH2COCl) in the presence of AlCl3. This is a Friedel-Crafts acylation reaction, which introduces an acyl group onto the benzene ring. The product (compound A) will be an aromatic ketone.
Step 2: Understand the mechanism of Friedel-Crafts acylation. AlCl3 acts as a Lewis acid, facilitating the generation of the acylium ion (CH3CH2CO+), which is the electrophile. This electrophile reacts with benzene to form compound A.
Step 3: Analyze the second reaction. Compound A undergoes nitration, which involves the reaction of HNO3 and H2SO4. This is an electrophilic aromatic substitution reaction where a nitro group (-NO2) is introduced onto the aromatic ring.
Step 4: Understand the regioselectivity of nitration. The acyl group on compound A is an electron-withdrawing group, which directs the incoming nitro group to the meta position relative to the acyl group.
Step 5: Combine the information from both reactions. Compound A is an aromatic ketone formed by Friedel-Crafts acylation, and compound B is the meta-nitro derivative of compound A formed by nitration.
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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 in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for understanding how compounds like benzene can be transformed into more complex structures, such as compound A in the given reaction. The stability of the aromatic system allows for the substitution to occur without disrupting the aromaticity.
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EAS Review
Friedel-Crafts Acylation
Friedel-Crafts acylation is a specific type of electrophilic aromatic substitution that introduces an acyl group into an aromatic ring. In the reaction shown, benzene reacts with an acyl chloride in the presence of a Lewis acid catalyst (AlCl3) to form compound A. This reaction is significant for synthesizing ketones and modifying aromatic compounds.
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Nitration of Aromatic Compounds
Nitration is a chemical process that introduces a nitro group (-NO2) into an aromatic compound, typically using a mixture of nitric acid (HNO3) and sulfuric acid (H2SO4). In the context of the question, compound A undergoes nitration to form compound B. This reaction is important for creating compounds that can participate in further chemical transformations and is a key step in the synthesis of various pharmaceuticals and explosives.
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Related Practice
Textbook Question
The following compound reacts with a hot, concentrated solution of NaOH (in a sealed tube) to give a mixture of two products. Propose structures for these products, and give a mechanism to account for their formation.
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Textbook Question
Give the structures of compounds A through C in the following series of reactions.
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Textbook Question
Give the structures of compounds C through D in the following series of reactions.
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Textbook Question
What products would you expect from the following coupling reactions?
(d)
(e)
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Textbook Question
A student added 3-phenylpropanoic acid (PhCH2CH2COOH) to a molten salt consisting of a 1:1 mixture of NaCl and AlCl3 maintained at 170 °C. After 5 minutes, he poured the molten mixture into water and extracted it into dichloromethane. Evaporation of the dichloromethane gave a 96% yield of the product whose spectra follow. The mass spectrum of the product shows a molecular ion at m/z 132. What is the product?
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