Chapter 5: Q.22 (page 195)
If the two stereogenic centers of a compound are R,S in configuration, what are the R,S assignments for its enantiomer and two diastereomers?
R, R for enantiomers.
R, R and S, S for diastereomers.
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Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopenatane.
What is the ee for each of the following mixtures of enantiomers A and B?
a. 95% A and 5% B
b. 85% A and 15% B
Draw both enantiomers for each biologically active compound.
amphetamine
(a powerful central nervous stimulant)
a.
ketoprofen
(analgesic and anti-inflammatory agent)
b.
The amino acid (S)-alanine has the physical characteristics listed under the structure.
a. What is the melting point of (R)-alanine?
b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?
c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?
d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?
e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.
Draw the structure of (S)-citalopram, a drug used to treat depression and anxiety that is much more potent than its R enantiomer.
citalopram
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