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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Textbook Question
Chapter 18, Problem 18.36P
Isoniazid, a drug used to treat tuberculosis, is prepared from pyridine-4-
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Acetals are formed from the reaction of two alcohols with a carbonyl under acidic
conditions. Acetal formation is faster with 1,2-ethanediol than with two methanol
molecules.
Choose the factor that explains the difference in reaction rates.
A) The reaction with 1,2-ethanediol has a
lower AH (enthalpy) of reaction.
B) The reaction with 1,2-ethanediol has a
higher AH (enthalpy) of reaction.
C) The reaction with 1,2-ethanediol has a
more favorable entropy of reaction.
What two enols are formed when pent-2-yne is treated with H2O, H2SO4, and HgSO4? Draw the ketones formed from these enols after tautomerization.
Prostaglandins are a class of cicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues.
They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20-
carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a
cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins.
Rate of formation of PGG2 with 10 mg/ml
ibuprofen (mM/min)
Arachidonic
acid (mM)
Rate of formation
of PGG2 (mM/min)
0.190
12.3
0.228
13.9
0.342
17.5
0.570
1.33
22.2
28.8
7.71
8.88
11.9
16.3
24.0
The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing
here on the first two columns, determine the Vmax and Km of the enzyme.
Vmax =
Km
mM/min
mM
Chapter 18 Solutions
Organic Chemistry
Ch. 18.1 - Prob. 18.1PCh. 18.2 - Prob. 18.2PCh. 18.4 - Prob. 18.3PCh. 18.4 - Prob. 18.4PCh. 18.4 - Synthesis of nitriles by nucleophilic displacement...Ch. 18.5 - Complete the following transesterification...Ch. 18.6 - Complete and balance equations for the following...Ch. 18.8 - Prob. AQCh. 18.8 - Several compounds have been found to inhibit...Ch. 18.8 - Prob. CQ
Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Prob. 18.8PCh. 18.9 - Prob. 18.9PCh. 18.10 - Prob. 18.10PCh. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Prob. 18.12PCh. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Prob. 18.14PCh. 18 - Prob. 18.15PCh. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Prob. 18.20PCh. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Prob. 18.23PCh. 18 - Prob. 18.24PCh. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Prob. 18.29PCh. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Prob. 18.31PCh. 18 - Prob. 18.32PCh. 18 - Prob. 18.33PCh. 18 - Prob. 18.34PCh. 18 - Prob. 18.35PCh. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Prob. 18.37PCh. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Prob. 18.39PCh. 18 - Prob. 18.40PCh. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Prob. 18.42PCh. 18 - The following sequence of steps converts...Ch. 18 - Prob. 18.44PCh. 18 - Prob. 18.45PCh. 18 - Prob. 18.46PCh. 18 - Prob. 18.47PCh. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Prob. 18.50PCh. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Prob. 18.52PCh. 18 - Prob. 18.53PCh. 18 - Prob. 18.54PCh. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Prob. 18.56PCh. 18 - Prob. 18.57PCh. 18 - Prob. 18.58PCh. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Prob. 18.71P
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