Organic Chemistry
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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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

-H,-CH3,-NH2,-OH,-SH,-Cl,-Br,-IIncreasingpriority

  • When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center

-CH2H,-CH2CH3,-CH2NH2,-CH2OH,-CH2ClIncreasingpriority

  • Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.

For example,

Organic Chemistry, Chapter 3, Problem 3.23P

  • 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 Ephedra sinica, the source of ephedrine, a potent bronchodilator. HO H CH3 Ephedrine [a -41
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