Could some answer this question. Im stuck on it. Thanks

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

A)Spontaneous creation of a carbocation and SO2 Cl, the ion pair created by SoCl's mechanism of action

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

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  1. Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite, actually forming an intimate ion pair. The second step is the concerted loss of a sulfur dioxide molecule and its replacement by the chloride, which was attached to the sulfite group. SO not A) and hence not E).

    B) is not correct as the leaving group is sulfite.

    C)(some circumstances) and D) are correct.

    This is an example of an SNi reaction. The important thing not mentioned in your list is retention of configuration.

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