5.57 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?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter17: Carboxylic Acids
Section: Chapter Questions
Problem 17.9P
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5.57 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?
Transcribed Image Text:5.57 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?
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