Im stuck on this question.

Question

The unusual aspect of functional group replacement of an alcohols hydroxyl group by chlorine by treatment with thionyl chloride is:

A)spontaneous creation of a carboccation and SO2 Cl,the ion pair created by SOCl's mechanism of action.

B)That oxygen, a more electronegetive atom could be replaced by chlorine, which is less electronegetive then oxygen.

C)That SOCl2 can replace the OH of a 3° alcohol

D)That SOCl2 can replace the OH of a 1° alcohol

E) All of the above

Answer 1

I am sure I have answered this already. Thionyl chloride to replace an OH group is an SNi reaction.

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