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Stereochemistry Question

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Stereochemistry Question

Post  highl on Mon Dec 09, 2013 2:59 am

I have the following multiple choice question that I am confused about:

When optically pure (R)-2-iodooctane is stirred with sodium iodide in acetone, the product will be:
a) optically pure (R)-2-iodooctane
b) optically pure (S)-2-octanol
c) optically pure (S)-2-iodooctane
d) racemic 2-iodooctance

I thought it would be c since the reaction would proceed by Sn2 which gives inversion but it is not the right answer. Any help here?
Thanks in advance!

highl

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