Chem 3590 Spring 2014 Quick guide for determining absolute configuration when multiple bonds are present

this is the stereocenter H3C D H H CH3 H H H

First write down the four substituents at the stereocenter. They are: Hydrogen group H lowest atomic number and mass Deuterium group D lowest atomic number/higher mass Isopropyl group C ? Vinyl group C ?

priority 4 priority 3 priority 1 or 2 priority 1 or 2

In order to figure whether the isopropyl group or the vinyl group has the highest priority, you must first list the atoms of the carbon in order of decreasing priority.
this carbon is: C C H H3C D H H CH3 H H H this carbon is: C Co H (and not: Co Co H )

The subscript zero here indicates that the carbon is duplicated. Only use the duplicated subscript zero once (NOT TWICE) if you are dealing with a double bond. Sometimes the atom in question is called a phantom atom. In this case, a phantom carbon. Now you realize that the lists are exactly the same. The fact that one of the carbons is a phantom atom makes no difference AT THIS POINT. So you have to pick the highest priority species atom in the two lists and generate two new priority lists.
this carbon is: C C H H3C D H H H H H CH3 H H H this carbon is: C Co H (and not: Co Co H )

Co H H

It should be clear from these two new lists that the vinyl group takes higher priority than the isopropyl group. In this example, we never got far enough to compare the second carbon in the isopropyl group with the second phantom carbon in the vinyl group. So, a phantom atom has no substituents which makes a phantom carbon of lower priority than any other type of carbon, even a methyl group.