Answered: Show how to convert amines to other…

Show how to convert amines to other functional groups, and devise multistepsyntheses using amines as starting materials and intermediates

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter16: Amines And Amides

Section: Chapter Questions

Problem 16.68E

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Question

Show how to convert amines to other functional groups, and devise multistep
syntheses using amines as starting materials and intermediates

Definition Definition Group of atoms that shape the chemical characteristics of a molecule. The behavior of a functional group is uniform in undergoing comparable chemical reactions, regardless of the other constituents of the molecule. Functional groups aid in the classification and anticipation of reactivity of organic molecules.

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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
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