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In the 1880's, Acetanilide, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. Part 1: Show a detailed arrow pushing mechanism of the acid catalyzed hydrolysis of acetanilide to aniline Part 2: Propose a synthesis of Acetaminophen from phenol. NH NH NH Phenacetin inophen Acetanilide Attach File Browse Local Files Browse Content Collection

In the 1880's, Acetanilide, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. Part 1: Show a detailed arrow pushing mechanism of the acid catalyzed hydrolysis of acetanilide to aniline Part 2: Propose a synthesis of Acetaminophen from phenol. NH NH NH Phenacetin inophen Acetanilide Attach File Browse Local Files Browse Content Collection

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
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**In the 1880s, Acetanilide**, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. **Part 1:** Show a detailed arrow pushing mechanism of the acid-catalyzed hydrolysis of acetanilide to aniline. **Part 2:** Propose a synthesis of Acetaminophen from phenol. **Chemical Structures:** 1. **Acetanilide**: - Structure shown: A benzene ring with an acetamido group attached. 2. **Phenacetin**: - Structure shown: A benzene ring with an ethoxy and an acetamido group. 3. **Acetaminophen**: - Structure shown: A benzene ring with an acetamido and a hydroxyl group. **Buttons for Further Action:** - Attach File - Browse Local Files - Browse Content Collection
Transcribed Image Text:**In the 1880s, Acetanilide**, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. **Part 1:** Show a detailed arrow pushing mechanism of the acid-catalyzed hydrolysis of acetanilide to aniline. **Part 2:** Propose a synthesis of Acetaminophen from phenol. **Chemical Structures:** 1. **Acetanilide**: - Structure shown: A benzene ring with an acetamido group attached. 2. **Phenacetin**: - Structure shown: A benzene ring with an ethoxy and an acetamido group. 3. **Acetaminophen**: - Structure shown: A benzene ring with an acetamido and a hydroxyl group. **Buttons for Further Action:** - Attach File - Browse Local Files - Browse Content Collection
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