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Topic: Synthesis of (S)-2-Phenylpropanenitrile  (Read 3898 times)

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Offline amcavoy

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Synthesis of (S)-2-Phenylpropanenitrile
« on: December 04, 2007, 04:39:04 PM »
I need to find the a synthesis of (S)-2-phenylpropanenitrile from (R)-1-bromo-1-phenylethane.  I was able to do something similar to this, but it's not the same.  I have included this as an attached image.  Is my idea on the right track or do I need to do something completely different?

Thank you.

Offline agrobert

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Re: Synthesis of (S)-2-Phenylpropanenitrile
« Reply #1 on: December 04, 2007, 08:17:55 PM »
You can synthesize (S)-2-phenylpropanenitrile from (R)-1-bromo-1-phenylethane using Kolbe Nitrile Synthesis

http://en.wikipedia.org/wiki/Kolbe_nitrile_synthesis

http://www.organic-chemistry.org/namedreactions/kolbe-nitrile-synthesis.shtm

You need a polar solvent that will solvate K+ to allow -CN to attack.  I don't how well SN2 displacement will occur because you are attacking a benzylic carbon.  It is possible to form phenyl ethene by E2 elimination.
In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur

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