Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 22, Problem 22.16P
Interpretation Introduction
Interpretation:
N-phenylacetamide is less reactive toward electrophilic
Expert Solution & Answer
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Students have asked these similar questions
How do you account for the fact that N-phenylacetamide (acetanilide) is less reactive
toward electrophilic aromatic substitution than is aniline?
-NHCCH,
-NH,
N-Phenylacetamide
(Acetanilide)
Aniline
Explain why a secondary amine forms a nitrosamine rather than a diazonium ion when it reacts with a nitrosonium ion.
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
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Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 22.1PCh. 22.1 - Write a structural formula for the product from...Ch. 22.1 - Prob. 22.3PCh. 22.2 - Prob. 22.4PCh. 22.2 - Predict the major produce(s) of each electrophilic...Ch. 22.3 - In SN2 reactions of haloalkanes, the order of...Ch. 22 - Prob. 22.8PCh. 22 - Prob. 22.9PCh. 22 - Addition of m-xylene to the strongly acidic...Ch. 22 - Addition of tert-butylbenzene to the strongly...
Ch. 22 - What product do you predict from the reaction of...Ch. 22 - Other groups besides H+ can act as leaving groups...Ch. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Suggest a reason why the nitroso group, N=O, is...Ch. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - The following molecules each contain two aromatic...Ch. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - The insecticide DDT is prepared by the following...Ch. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.32PCh. 22 - Show how to prepare each compound from...Ch. 22 - Prob. 22.34PCh. 22 - Show reagents and conditions to bring about the...Ch. 22 - Prob. 22.36PCh. 22 - Propose a synthesis for each compound from...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Cancer of the prostate is the second leading cause...Ch. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - When certain aromatic compounds are treated with...Ch. 22 - Prob. 22.49PCh. 22 - Following is the structure of miconazole, the...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Show how the antidepressant venlafaxine (Effexor)...Ch. 22 - Prob. 22.57PCh. 22 - Given this retrosynthetic analysis, propose a...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - A newer generation of antipsychotics, among them...Ch. 22 - Prob. 22.63P
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- When acetophenone, hydroxelamine hydrochloride, and sodium hydroxide are reacted to synthesize acetophenone oxime, why is it necessary to add hydrochloric acid after the reaction to make it acidic?arrow_forwardIn the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =arrow_forwardWhy is methyl salicylate so easily absorbed through the skin?arrow_forward
- 6. The reaction between aniline and nitrous acid at low temperature yields A) an N-nitroso amine B) a diazonium salt C) a nitrile D) an amine nitrite salt 7. An organic nitrogen compound, X, gives ammonia on warming with dilute aqueous sodium hydroxide, X could be A) ethanamide B) ethylamine C) phenylamine D) amino ethanoic acidarrow_forward1. What are the chemical hazards of both aniline and acetic anhydride? 2. What are the medicinal and industrial uses/application of acetanilide? 3. What was the undesirable effect of acetanilide that made it toxic? 4. How does acetanilide produce an analgesic effect in the body?arrow_forwardWrite the mechanism for the following reactions: 1. the acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine 2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine a. How do the two mechanisms differ?arrow_forward
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