Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 25, Problem 25.11P
Interpretation Introduction
a.
Interpretation:
Why the substitution of sulfur for oxygen is important when studying the stereochemistry of the F16BP-catalyzed hydrolysis of
Concept Introduction:
An atom that contains four different atoms/groups around is called the chiral center. Oxygen atom has three isotopes. It becomes difficult to study the stereochemical reactions when the nucleophile is water.
Interpretation Introduction
b.
Interpretation:
Assuming that the substitution of sulfur for oxygen does not change the mechanism of the reaction, the product of the reaction is to be determined along with its stereochemistry.
Concept Introduction:
The mechanism of F16BP is described in Fig. 25.5, text p. 1302. Assuming inversion of configuration, the product of the reaction and its stereochemistry is shown below:
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The synthesis of carbohydrates can be particularly difficult because of the large
number of chiral centers and OH functional groups present. Epoxides can be
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the reaction of a phenyl Gilman reagent with this epoxide.
A
• Use the wedge/hash bond tools to indicate stereochemistry where it
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• Explicitly define the cis/trans stereochemistry of fused rings using
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The synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic
intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide.
QAO
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds.
• If enantiomers are formed, draw both.
• Separate multiple products using the sign from the drop-down menu.
+
e./
8)
16224
000. It
a. (S)-Penicillamine, an amino acid that does not occur in proteins, is used as a copper chelating agent to treat Wilson's disease, an inherited defect in copper metabolism. (R)-Penicillamine is toxic, sometimes causing blindness. Draw the structures of (R)- and (S)- penicillamine. b. What disulfide is formed from oxidation of (S)-penicillamine?
Chapter 25 Solutions
Organic Chemistry
Ch. 25 - Prob. 25.1PCh. 25 - Prob. 25.2PCh. 25 - Prob. 25.3PCh. 25 - Prob. 25.4PCh. 25 - Prob. 25.5PCh. 25 - Prob. 25.6PCh. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Prob. 25.9PCh. 25 - Prob. 25.10P
Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Prob. 25.19PCh. 25 - Prob. 25.20PCh. 25 - Prob. 25.21APCh. 25 - Prob. 25.22APCh. 25 - Prob. 25.23APCh. 25 - Prob. 25.24APCh. 25 - Prob. 25.25APCh. 25 - Prob. 25.26APCh. 25 - Prob. 25.27APCh. 25 - Prob. 25.28APCh. 25 - Prob. 25.29APCh. 25 - Prob. 25.30APCh. 25 - Prob. 25.31APCh. 25 - Prob. 25.32APCh. 25 - Prob. 25.33APCh. 25 - Prob. 25.34APCh. 25 - Prob. 25.35APCh. 25 - Prob. 25.36APCh. 25 - Prob. 25.37APCh. 25 - Prob. 25.38APCh. 25 - Prob. 25.39APCh. 25 - Prob. 25.40AP
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