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 3, Problem 3.23P
Interpretation Introduction
Interpretation:
The configuration of the each chiral center has to be given for ephedrine molecule.
Concept Introduction:
Priority rules:
- Priorities based on
atomic number
- When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center
- Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.
For example,
- Priority assignment is made at the first point of difference between groups (should not be based on the larger group).
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For centuries, Chinese herbal medicine has used extracts of Ephedra sinica to treat asthma.
Ephedra as an"herbal supplement" has been implicated in the deaths of several athletes
and has recently been banned as a dietary supplement. Phytochemical investigation of
this plant resulted in isolation of ephedrine, a very potent dilator of the air passages of
the lungs. Ephedrine also has profound effects on the cardiovascular system. The natu-
rally occurring stereoisomer is levorotatory and has the following structure. Assign an
Ror S configuration to each chiral center.
H
NHCH3
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HO
H
CH3
Ephedrine [a -41
#23
The shrub ma huang (Section 5.4A) contains two biologically active stereoisomers—ephedrine and pseudoephedrine—with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once-popular combination drug used by body builders to increase energy and alertness, whereas pseudoephedrine is a nasal decongestant.
a.Draw the structure of naturally occurring (−)-ephedrine, which has the 1R,2S configuration.
b.Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2S configuration.
c.How are ephedrine and pseudoephedrine related?
d.Draw all other stereoisomers of (−)-ephedrine and (+)pseudoephedrine, and give the R,S designation for all stereogenic centers.
e.How is each compound drawn in part (d) related to (−)-ephedrine?
Chapter 3 Solutions
Organic Chemistry
Ch. 3.2 - Prob. 3.1PCh. 3.3 - Assign priorities to the groups in each set. (a)...Ch. 3.3 - Prob. 3.3PCh. 3.4 - Following are stereorepresentations for the four...Ch. 3.4 - Prob. 3.5PCh. 3.4 - Prob. 3.6PCh. 3.5 - How many stereoisomers exist for...Ch. 3.5 - How many stereoisomers exist for...Ch. 3.7 - Prob. 3.9PCh. 3.7 - Prob. 3.10P
Ch. 3.8 - If the side chain of the amino add is a methyl...Ch. 3.8 - Prob. BQCh. 3.8 - The amino acids cysteine and serine are shown....Ch. 3.8 - Prob. DQCh. 3.8 - As stated, proteins are stereochemically pure...Ch. 3.8 - As stated, proteins are stereochemically pure...Ch. 3 - Prob. 3.11PCh. 3 - One reason we can be sure that sp3-hybridized...Ch. 3 - Which compounds contain chiral centers? (a)...Ch. 3 - Prob. 3.15PCh. 3 - Prob. 3.16PCh. 3 - Prob. 3.17PCh. 3 - Mark each chiral center in the following molecules...Ch. 3 - Prob. 3.19PCh. 3 - Assign priorities to the groups in each set. (a) H...Ch. 3 - Following are structural formulas for the...Ch. 3 - Following is a staggered conformation for one of...Ch. 3 - Prob. 3.23PCh. 3 - When oxaloacetic acid and acetyl-coenzyme A...Ch. 3 - Prob. 3.25PCh. 3 - Mark each chiral center in the following molecules...Ch. 3 - Prob. 3.27PCh. 3 - Prob. 3.28PCh. 3 - Prob. 3.29PCh. 3 - Prob. 3.30PCh. 3 - Which of the following are meso compounds?Ch. 3 - Prob. 3.32PCh. 3 - Prob. 3.33PCh. 3 - Which of the following compounds are chiral?...Ch. 3 - Prob. 3.35PCh. 3 - Prob. 3.36PCh. 3 - Prob. 3.37PCh. 3 - The chiral catalyst (R)-BINAP-Ru is used to...Ch. 3 - Prob. 3.39P
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