Naming Stereoisomers

Absolute Configuration and Stereochemical Nomenclature

	On the previous page, we referred to the two stereoisomers of 2-bromobutane, simply as "A" and "B". Chemists have devised a systematic way of naming stereoisomers, based on the concept of absolute configuration.


	The absolute configuration around a chiral center is designated as either "R" or "S".

	These designations come from the Latin for left and right handed...

	(R) from rectus for right-handed and (S) from sinister for left-handed

	The (R) or (S) designation is added to the IUPAC name of the compound as follows:

	The absolute configuration around the chiral center in Isomer A is the "S" configuration.

	Thus, this compound is (S)-2-bromobutane.

	Isomer B has the opposite or "R" configuration.

	This compound is (R)-2-bromobutane.

	The absolute configuration around a stereocenter is determined using the Cahn-Ingold-Prelog rules (named after the chemists who defined them):


	Rule #1 --	Identify all four substituants at the chiral center under examination


	Rule #2 --	Assign priorities to substituants by looking at the atoms attached directly to chiral center.


		The higher the atomic number the higher priority (use atomic mass for isotopes of same element).

		In assigning priorties, follow each substituant away from the chiral center until a point of difference is found.

	Rule #3 --	Orient molecule with the lowest priority group pointed away from you.


	Rule #4 --	Trace the remaining three groups numerically (i.e. from highest to lowest priority).


		If the trace goes to the right (or clockwise) the absolute configuration is (R).

		If the trace goes to the left (or counterclockwise) the absolute configuration is (S).

	It is probably easier to show an example than to explain. So consider the two isomers of 2-bromobutane.


	Identify the substituants on the chiral center (Rule #1) and assign priorities (Rule #2):


	Rotate molecule so that the lowest priority group (the -H in this case) is in the back (Rule #3) and trace the remaining three substituants in numerical order (Rule #4).

	Here are the "live" images of the two compounds, rotate them until the -H on the stereocenter is in the back.

	Isomer A
	should look something like this:

	Since the trace goes counter clockwise, this is the (S) isomer.

	Isomer B
	should look something like this:

	Since the trace goes clockwise this is the (R) isomer.

Last Update: 12-Mar-2007