C9. Stereochemistry Flashcards
In the case of multiple stereogenic centres, how do you calculate the number of alternative configurations?
2 to the power of n: n is the number of stereogenic centres ONE NOTE
What are diastereoisomers (diastereomers)?
Stereoisomers which are not enantiomers are called
diastereoisomers (diastereomers)
enantiomer?
pairs of compounds with exactly the same connectivity but opposite 3D shapes e.g 1R 2S and 1S 2R
How to draw an enantiomer?
draw exact mirror image or draw the groups in the opposite orientation ONE NOTE
relationship between conformation and configuration?
change in conformation does not affect configuration
diastereomer?
type of stereoisomer that is not another mirror image of another stereoisomer of the same compound e.g 1R 2S and 1R 2R or 1S 2S ONE NOTE
what is a 2- epimer?
a sugar that differs from another sugar in the configuration at the second carbon atom e.g 1R 2S and 1R 1R
what is a 1- epimer?
a sugar that differs from another sugar in the configuration at the first carbon atom e.g 1R 2S and 1S 1S ONE NOTE
Describe the properties of enantiomers?
Enantiomers are chemically
identical except in optical
properties, e.g. (–)- and (+)-
ephedrine. Biological
properties may be different
Describe properties of diastereoisomers
Diastereoisomers have
different physical and
chemical properties, e.g. (–)- ephedrine and (–)-
pseudoephedrine