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Posted by on Thursday, April 21, 2011 at 8:50am.

Could someone help out with this question. Im stuck on it. Thanks

When (R)-butan-2-ol is treated with TsCl in pyridine and the tosylated alcohol is treated with sodium chloride in acetone, the resulting product is:

A) (R)-2-iodobutane
B) (S)-2-iodobutane
C) 2-iodobutane (racemic)
D) 1-butane
E) None of these

I think its choice B or C, but im not sure.

  • Chemistry - , Thursday, April 21, 2011 at 9:55am

    When (R)-butan-2-ol is treated with TsCl in pyridine and the tosylated alcohol is treated with sodium chloride in acetone we expect an inversion of the chiral centre and a 2-chlorobutane to be formed. There is no 2-chlorobutane in the list so
    E)none of these.

    There will also be some elimination reaction to form butene, but again there is no butene in the list.

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