If a molecule contains #n# chiral centres, how many stereoisomers are possible?

1 Answer
Jun 15, 2017

If there are #n# chiral centres, there are #2^n# stereoisomers......

Explanation:

There is of course a catch, and it is illustrated by a simple organic molecule, #"2,3-butandiol...."#

#H_3stackrel(1)C-stackrel(2)CH(OH)stackrel(3)CH(OH)stackrel(4)CH_3#

We look at the molecule and #C2# and #C3# ARE POTENTIALLY CHIRAL (do you agree?), and each carbon has 2 optical antipodes, so that we could potentially form #"RR"# and #"SS"# and #"RS"# and #"SR"# stereoisomers (i.e. in accord with the rule proposed). #"RR"# and #"SS"# share an enantiomeric relationship, but share a DIASTEREOMERIC relationship with #"RS"# and #"SR"#.

However, for this example, the #"RS"# and #"SR"# stereoisomers are SUPERPOSABLE mirror images; these are example of optically inactive #"meso"# isomers.

Mind you, a compound with more than 2 chiral centres will be rather difficult to synthesize in optically pure forms. You should not have to consider structures with MORE than 2 stereocentres. Why not? Because these questions are as difficult to mark as they are to answer. And please don't forget the utility of using a model set to gain understanding of stereochemistry.