Im stuck on this 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

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

To determine the correct answer, let's break down each choice and analyze them:

A) The statement talks about the mechanism of thionyl chloride (SOCl2) and its ability to create a carbocation and SO2Cl ion pair. However, this is not specifically related to the unusual aspect of functional group replacement.

B) This statement mentions the replacement of oxygen (O) by chlorine (Cl) in terms of electronegativity. While it is true that chlorine is less electronegative than oxygen, this is not the unusual aspect of functional group replacement using thionyl chloride.

C) This statement suggests that thionyl chloride (SOCl2) can replace the hydroxyl group (OH) of a tertiary (3°) alcohol. This is a correct statement, as thionyl chloride is often used to substitute the hydroxyl group in the presence of a tertiary alcohol.

D) This statement suggests that thionyl chloride (SOCl2) can replace the hydroxyl group (OH) of a primary (1°) alcohol. This is also a correct statement, as thionyl chloride can react with primary alcohols to form alkyl chlorides.

E) "All of the above" includes all the statements mentioned in choices A, B, C, and D. While choices A, C, and D are correct, choice B does not specifically address the unusual aspect of functional group replacement.

Therefore, the correct answer is:

C) That SOCl2 can replace the OH of a 3° alcohol and D) That SOCl2 can replace the OH of a 1° alcohol.