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To: tommysdad who wrote (4591)10/20/2000 10:20:46 AM
From: jayhawk969  Read Replies (1) | Respond to of 10280
 
Slightly off topic:

It has been over 30 years since I took Organic Chemistry. I am not sure I want to go back and relearn it.

There are some reactions referred to enantioselective reactions where one enantiomer is produced in excess of the other primarily because one side of the reactant
molecule or intermediate was hindered so that side of access was less likely than the less hindered side. Such a mixture of two enantiomers will show an optical
rotation. We can determine the specific rotation of the mixture and then knowing the specific rotation of the enantiomer in excess we can determine the enantiomeric
excess.

enantiomeric excess = (specific rotation of the mixture/ specific rotation of the pure enantiomer in excess) 100

The enantiomeric excess can be determined in another way if we know the amount of each enantiomer produced. If one knows the moles of each enantiomer
produced then:

enantiomeric excess = (moles of major enantiomer - moles of other enantiomer / Total moles of both enantiomers) 100

Let's work a problem determining enantiomeric excess. Let's suppose that we have a reaction mixture which we measure for rotation, and the observed specific
rotation of the reaction mixture is measured to be +8.52 degrees of rotation. The specific rotation of the S-configured enantiomer was said to be -15.00 degrees of
rotation. Determine the enantiomeric excess.

The sign on the specific rotation of the mixture tells us which enantiomer is in excess. Since the pure S-Configured isomer was measured to be -15.00 degrees, then
the R-configured isomer would be +15.00 degrees. The positive sign on the observed specific rotation of the mixture tells us that the R-configured isomer is in
excess. So the enantiomeric excess would be:

enantiomeric excess = (+8.52 / +15.00)(100) = 56.8 % in excess of R-isomer

This means that 56.8% of the entire mixture is in excess of the R-configured isomer.