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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Draw both enantiomers for each biologically active compound.
amphetamine
(a powerful central nervous stimulant)
a.
ketoprofen
(analgesic and anti-inflammatory agent)
b.
Draw both enantiomers of clopidogrel (trade name Plavix), a drug given to prevent the formation of blood clots in persons who have a history of stroke or coronary artery disease. Plavix is sold as a single enantiomer with the S configuration. Which enantiomer is Plavix?
A limited number of chiral compounds having no stereogenic centers exist. For example, although A is achiral, constitutional isomer B is chiral. Make models and explain this observation. Compounds containing two double bonds that share a single carbon atom are called allenes. Locate the allene in the antibiotic mycomycin and decide whether mycomycin is chiral or achiral.
Drawn are four isomeric dimethylcyclopropanes.
a. How are the compounds in each pair related (enantiomers, diastereomers, constitutional isomers): A and B; A and C; B and C; C and D?
b. Label each compound as chiral or achiral.
c. Which compounds, alone, would be optically active?
d. Which compounds have a plane of symmetry?
e. How do the boiling points of the compounds in each pair compare: A and B; B and C; C and D?
f. Which of the compounds are meso compounds?
g. Would an equal mixture of compounds C and D be optically active? What about an equal mixture of B and C?
Draw the enantiomer and a diastereomer for each compound.
a.
b.
c.
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