ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
Author: SMITH
Publisher: MCG
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Chapter 5, Problem 52P
Interpretation Introduction
Interpretation: The structure of
Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.
The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.
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Draw the structure of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potent than any of its other stereoisomers.
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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 5 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)
Ch. 5.1 - Prob. 1PCh. 5.2 - Prob. 2PCh. 5.3 - Draw the mirror image of each compound. Label each...Ch. 5.3 - Prob. 4PCh. 5.3 - A molecule is achiral if it has a plane of...Ch. 5.6 - Prob. 17PCh. 5.6 - Prob. 18PCh. 5.7 - Prob. 19PCh. 5.7 - Prob. 20PCh. 5.7 - Problem 5.18 Compounds E and F are two isomers of...
Ch. 5.8 - Prob. 22PCh. 5.8 - Prob. 23PCh. 5.8 - Prob. 24PCh. 5.9 - Prob. 25PCh. 5.9 - Prob. 26PCh. 5.9 - Prob. 27PCh. 5.10 - Which of the following cyclic molecules are meso...Ch. 5.10 - Prob. 29PCh. 5.11 - Prob. 30PCh. 5.12 - Problem 5.28 The amino acid has the physical...Ch. 5.12 - Prob. 32PCh. 5.12 - Prob. 33PCh. 5.12 - Prob. 34PCh. 5.12 - Prob. 35PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - Prob. 41PCh. 5 - Prob. 42PCh. 5 - 5.40 Determine if each compound is identical to or...Ch. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - Prob. 48PCh. 5 - Prob. 52PCh. 5 - Prob. 56PCh. 5 - Prob. 61PCh. 5 - Prob. 67PCh. 5 - Prob. 68PCh. 5 - Prob. 69PCh. 5 -
5.67 Artemisinin and mefloquine are widely used...Ch. 5 - 5.68 Saquinavir (trade name Invirase) is a...Ch. 5 - Prob. 72P
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