Textbook Question
Give the structures of compounds A through B in the following series of reactions.
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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 57d
Give the structures of compounds C through D in the following series of reactions.
Verified step by step guidance1
Step 1: Analyze the first reaction. The benzene ring reacts with an acyl chloride (CH3CH2COCl) in the presence of AlCl3, a Lewis acid catalyst. This is a Friedel-Crafts acylation reaction, which introduces an acyl group (CH3CH2CO-) onto the benzene ring, forming compound A.
Step 2: Examine the second reaction. Compound A undergoes nitration using HNO3 and H2SO4. This introduces a nitro group (-NO2) onto the benzene ring, typically at the meta position relative to the acyl group due to the electron-withdrawing nature of the acyl group, forming compound B.
Step 3: Consider the third reaction. Compound B is treated with Zn(Hg) and HCl, which is a Clemmensen reduction. This reduces the acyl group (CH3CH2CO-) to an alkyl group (CH3CH2-), forming compound C.
Step 4: Analyze the final reaction. Compound C is oxidized using hot, concentrated KMnO4. This strong oxidizing agent converts the alkyl group (CH3CH2-) attached to the benzene ring into a carboxylic acid group (-COOH), forming compound D.
Step 5: Summarize the transformations. Compound A is formed via Friedel-Crafts acylation, compound B via nitration, compound C via Clemmensen reduction, and compound D via oxidation with KMnO4. Each step involves a specific functional group transformation on 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 in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In this reaction, the aromatic compound acts as a nucleophile, attacking the electrophile, which leads to the formation of a new bond. The presence of a catalyst, such as AlCl3, is often required to generate a more reactive electrophile, facilitating the substitution process.
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Reduction Reactions
Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In the context of organic chemistry, this often refers to the conversion of carbonyl compounds to alcohols or alkenes. The reaction shown with Zn(Hg) and HCl indicates a reduction process, where a carbonyl group is reduced to an alkane, typically through a Clemmensen reduction, which is useful for transforming ketones or aldehydes into hydrocarbons.
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Oxidation Reactions
Oxidation reactions in organic chemistry involve the loss of electrons or an increase in oxidation state, often resulting in the conversion of alcohols to carbonyl compounds or carboxylic acids. The use of KMnO4 in hot, concentrated conditions indicates a strong oxidizing environment, which can oxidize alcohols to carboxylic acids or aldehydes to carboxylic acids, depending on the starting material. This step is crucial for understanding the transformation from compound C to D in the reaction sequence.
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Related Practice
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Give the structures of compounds A through C in the following series of reactions.
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Show the products you expect when each compound reacts with NBS with light shining on the reaction.
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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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