ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582422
Author: Brown
Publisher: CENGAGE L
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Question
Chapter 22, Problem 22.16P
Interpretation Introduction
Interpretation:
N-phenylacetamide is less reactive toward electrophilic
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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
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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Can pyridine form a diazonium salt and can quinoline and isoquinoline undergo electrophilic substitution on the benzenoid ring but nucleophilic substitution on the nitrogen ring?
Chapter 22 Solutions
ORGANIC CHEMISTRY-OWL V2 ACCESS
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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- Predict the NMR spectra of Acetanilide, p-acetamidobenzene sulphonamide and p-aminobenzene sulphonamidearrow_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 the reaction of 1° amines with carbonyl compounds forms imines ?arrow_forward
- how to prepare phenylmethanamine from benzene ?arrow_forwardIllustrate the Separation of cyclohexanamine and cyclohexanol by an extraction procedure ?arrow_forwardShow the reaction mechanisms in converting benzophenone to benzopinacol to benzopinacolone. Why must the mixture of benzophenone and isopropyl alcohol with acid be exposed to sunlight? Suppose that the flask is coated with sunscreen, would the reaction work?arrow_forward
- Two reactions occur when sodium hydroxide is added to methyl salicylate. One is immediate and one only occurs with reflux over time. What type of reaction occurs immediately and with which functional group on methyl salicylate does it react? What type of reaction occurs with reflux over time and with which functional group on methyl salicylate does it react?arrow_forwardExplain why carboxylic acids do not undergo nucleophilic acyl substitution reactions with amines.arrow_forwardAlthough acetanilide and phenacetin are not appreciably acidic, aceta- minophen (like aspirin) is a stronger acid than water. What problem would you encounter if the unknown component were acetaminophen rather than acetanilide or phenacetin, and you extracted the aspirin with 5% NaOH? Explain, giving equations for any relevant reactions.arrow_forward
- Account for the experimental behavior of each class of amines (primary,secondary and tertiary) based on their relative reactivities with benzenesulfonyl chloride.arrow_forwardThe analgesic Tylenol is often taken by people who are allergic to aspirin. Tylenol contains acetaminophen (structure shown) as the active ingredient. Is the structure of acetaminophen similar to the structure of aspirin? In what way? Would acetaminophen give a positive phenol test? What products would be obtained if acetaminophen were hydrolyzed in acidic aqueous solution?arrow_forwardCompare the physical properties of acid derivatives, and explain the unusually highboiling points and melting points of amides. Compare the relative reactivity ofesters, thioesters, amides, nitriles, anhydrides, and acid chloridesarrow_forward
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