Question

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.

Answer 1

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.