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18.28 Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds. In some cases, there may be more than one plausible solution.

18.28 Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds. In some cases, there may be more than one plausible solution.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
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### Organic Chemistry: Benzene Synthesis Problems **Problem 18.28** Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds. In some cases, there may be more than one plausible solution. **Compounds:** - **(a)** - Structure: Benzene ring with a bromine (Br) atom in the meta position and a ketone group attached to the benzene ring. - **(b)** - Structure: Benzene ring with an amino (NH₂) group in the para position relative to a bromine (Br) atom and an ethyl group attached directly to the benzene ring. - **(c)** - Structure: Benzene ring with an amino (NH₂) group in the para position relative to a chlorine (Cl) atom and methyl (CH₃) groups attached to the benzene ring. - **(d)** - Structure: Benzene ring with a sulfonic acid (SO₃H) group in the para position relative to a bromine (Br) atom and a chlorine (Cl) atom in the meta position relative to a bromine atom. **Apply the Skill:** Design synthetic routes by considering the positions and reactivity of substituents on the benzene ring. Utilize common reagents and reactions such as nitration, halogenation, Friedel-Crafts alkylation/acylation, sulfonation, and reduction, among others, to achieve the desired target molecules. **Diagrams and Graphs Explanation:** 1. **Diagram (a):** - The benzene ring features a bromine (Br) atom in one meta position and a ketone (C=O) group attached directly to the ring. 2. **Diagram (b):** - The benzene ring features an amino (NH₂) group in the para position relative to a bromine (Br) atom, with an ethyl side chain attached directly to the benzene ring. 3. **Diagram (c):** - The benzene ring features an amino (NH₂) group in the para position relative to a chlorine (Cl) atom, with additional methyl (CH₃) groups attached directly to the benzene ring. 4. **Diagram (d):** - The benzene ring features a sulfonic acid (SO₃H
Transcribed Image Text:### Organic Chemistry: Benzene Synthesis Problems **Problem 18.28** Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds. In some cases, there may be more than one plausible solution. **Compounds:** - **(a)** - Structure: Benzene ring with a bromine (Br) atom in the meta position and a ketone group attached to the benzene ring. - **(b)** - Structure: Benzene ring with an amino (NH₂) group in the para position relative to a bromine (Br) atom and an ethyl group attached directly to the benzene ring. - **(c)** - Structure: Benzene ring with an amino (NH₂) group in the para position relative to a chlorine (Cl) atom and methyl (CH₃) groups attached to the benzene ring. - **(d)** - Structure: Benzene ring with a sulfonic acid (SO₃H) group in the para position relative to a bromine (Br) atom and a chlorine (Cl) atom in the meta position relative to a bromine atom. **Apply the Skill:** Design synthetic routes by considering the positions and reactivity of substituents on the benzene ring. Utilize common reagents and reactions such as nitration, halogenation, Friedel-Crafts alkylation/acylation, sulfonation, and reduction, among others, to achieve the desired target molecules. **Diagrams and Graphs Explanation:** 1. **Diagram (a):** - The benzene ring features a bromine (Br) atom in one meta position and a ketone (C=O) group attached directly to the ring. 2. **Diagram (b):** - The benzene ring features an amino (NH₂) group in the para position relative to a bromine (Br) atom, with an ethyl side chain attached directly to the benzene ring. 3. **Diagram (c):** - The benzene ring features an amino (NH₂) group in the para position relative to a chlorine (Cl) atom, with additional methyl (CH₃) groups attached directly to the benzene ring. 4. **Diagram (d):** - The benzene ring features a sulfonic acid (SO₃H
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