Free Radical Halogenation Module: Part 3: Stereoselectivity: Determining stereochemistry of carbon centers

Posted on October 2nd, 2013

This is the second part of a multi-part module on Free Radical Halogenation.

View the first part here: Part 1: The Mechanism

View the second part here: Part 2: Regioselectivity


Radial intermediates (step 2a product) produce an sp2-like hybridization orbital with the lone electron in the vacant 2p orbital, therfore attack of the radical electron on the C-H bond can take place from either side of the molecule.  The result will always produce an RACEMIC MIXTURE (or equal amount) of the two enantiomers.


Free Radical Halogenation Module Pic 6

There are multiple examples of this reaction to review in the Study Mode. When ready, test your knowledge in the Quiz Mode.

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Stay tuned for Part 4: Practice Quiz