CONNECT IA GENERAL ORGANIC&BIO CHEMISTRY
4th Edition
ISBN: 9781260562620
Author: SMITH
Publisher: MCG
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Chapter 17.8, Problem 17.19P
Interpretation Introduction
Interpretation:
The
Concept Introduction:
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What carboxylic acid and amine are needed to synthesize the pain reliever phenacetin? Phenacetin was once a component of the over-the-counter pain reliever APC (aspirin, phenacetin, caffeine), but it is no longer used because of its kidney toxicity.
Draw the struetre of the following three isomeic amides with chemical feruula CHNO.
Amide #1: (E)-N,N-dimethyl-2-butenamide
Amide #2: (7)-N-methyl-3-pentenamide
Amide #3: (7)-3-hexenamide
C'onsider Z sterenchemistry of alkenes.
• Draw one structure per sketcher. Add additional sketchers asing the drop-down memu in the hottom right comer.
Sepamte structares with - signs from the drop-down mena.
O00. IF
ChemDoodle
ChemDoodie
ChemDoodle
just the first one is what I could really use help
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Amide #1: (E)-N,N-dimethyl-2-butenamide
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 17 Solutions
CONNECT IA GENERAL ORGANIC&BIO CHEMISTRY
Ch. 17.1 - Draw out each compound to clearly show what groups...Ch. 17.1 - Prob. 17.2PCh. 17.1 - (a) Label each functional group in lisinopril, a...Ch. 17.2 - Give the IUPAC name for each compound. a. b. c.Ch. 17.2 - Give the structure corresponding to each IUPAC...Ch. 17.2 - Prob. 17.5PCh. 17.2 - Give an acceptable name for each ester. a. CH3(...Ch. 17.2 - Prob. 17.6PCh. 17.2 - Prob. 17.7PCh. 17.2 - Prob. 17.8P
Ch. 17.2 - Prob. 17.9PCh. 17.3 - Which compound in each pair has the higher boiling...Ch. 17.4 - Prob. 17.11PCh. 17.5 - In addition to ethyl butanoate (Section 17.5),...Ch. 17.6 - Prob. 17.3PPCh. 17.6 - Prob. 17.13PCh. 17.6 - Which compound ¡n each pair ¡s more water soluble?...Ch. 17.6 - Prob. 17.5PPCh. 17.6 - Prob. 17.14PCh. 17.6 - Prob. 17.15PCh. 17.7 - Ibuprofen is another pain reliever that is a...Ch. 17.8 - Prob. 17.6PPCh. 17.8 - Prob. 17.17PCh. 17.8 - Prob. 17.18PCh. 17.8 - Prob. 17.7PPCh. 17.8 - Prob. 17.19PCh. 17.9 - Prob. 17.8PPCh. 17.9 - Prob. 17.20PCh. 17.9 - Prob. 17.21PCh. 17.9 - Prob. 17.22PCh. 17.9 - Prob. 17.9PPCh. 17.9 - Prob. 17.23PCh. 17.9 - Prob. 17.24PCh. 17.10 - Prob. 17.10PPCh. 17.10 - Prob. 17.25PCh. 17.11 - Prob. 17.26PCh. 17 - Prob. 27PCh. 17 - Prob. 28PCh. 17 - Prob. 29PCh. 17 - Prob. 30PCh. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - Give an acceptable name for each ester. a. CH3CO2(...Ch. 17 - Prob. 37PCh. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Prob. 40PCh. 17 - Prob. 41PCh. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - Draw the structure corresponding to each name. a....Ch. 17 - Draw the structure corresponding to each name. a....Ch. 17 - Draw the structure corresponding to each name. a....Ch. 17 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Prob. 50PCh. 17 - Prob. 51PCh. 17 - Prob. 52PCh. 17 - Prob. 53PCh. 17 - Prob. 54PCh. 17 - What ester is formed when butanoic acid...Ch. 17 - Prob. 56PCh. 17 - Prob. 57PCh. 17 - Prob. 58PCh. 17 - Prob. 59PCh. 17 - Prob. 60PCh. 17 - Prob. 61PCh. 17 - Prob. 62PCh. 17 - Prob. 63PCh. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Prob. 66PCh. 17 - What products are formed when each ester is...Ch. 17 - Prob. 68PCh. 17 - Prob. 69PCh. 17 - Prob. 70PCh. 17 - Prob. 71PCh. 17 - Prob. 72PCh. 17 - Prob. 73PCh. 17 - Prob. 74PCh. 17 - Draw the products formed in each reaction. a. b....Ch. 17 - Draw the products formed in each reaction. a. b....Ch. 17 - Answer the following questions about A, depicted...Ch. 17 - Answer the following questions about B, depicted...Ch. 17 - Prob. 79PCh. 17 - Prob. 80PCh. 17 - Prob. 81PCh. 17 - Prob. 82PCh. 17 - Prob. 83PCh. 17 - Prob. 84PCh. 17 - Prob. 85PCh. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - Prob. 89CPCh. 17 - Lactams can be hydrolyzed with base, just like...
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