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Stereospecific versus stereoselective
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norahjane
#1 Posted : Tuesday, June 17, 2014 5:32:15 PM
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A reaction must be stereoselective if it is stereospecific, however not necessarily stereospecific if it is stereoselective - what is an example of a reaction that is stereoselective and NOT stereospecific?

I was thinking an example might be perhaps a reaction where there is steric hindrance, there would only be a particular product produced, yet it is possible that a different isomer could be produced IF there was no hindrance. Does anyone have a specific and better example of this that can explain the difference well?

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vanessalittle
#2 Posted : Wednesday, June 18, 2014 2:12:36 AM
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Hi there!

A specific example eludes me right now (though if I think of one, I'll post it!); but, generally speaking, for a reaction to be stereospecific, the reactant must first exist as a stereoisomer. Any reaction that starts with an achiral starting material, but produces a mixture of stereochemical products, of which one stereoisomer predominates, would be stereoselective but NOT stereospecific.

Hope this helps! I will keep digging for specific examples for you.

V
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