I'm trying to figure out how to make an arrow pushing representation of the hydrolysis of an alkyl hydrogen sulfate. So far, I cannot figure out how exactly to do it. I'm under the impression that the hydrolysis is perhaps a two-step reaction mechanism? I'm not sure, and I was hoping someone here could help me figure that out.
Attached is an image describing what I've found on the Internet, but I don't find it good enough.
It doesn't really say how the insertion of water breaks the sulfate bond; it gives the impression that the sulfate bond breaks itself. Furthermore, it seems as though that water then adds to the carbocation that remains.
The things represented in the attachment make me think that the hydrolysis of an alkyl hydrogen sulfate is two-step, but I have been told that it is a one-step, biomolecular reaction mechanism. The professor offered no drawing, though.
Could someone please draw a more accurate representation or an argument for one version or the other?
Diagram 1 = Overall reaction
Diagram 2 = Process 1 = addition of sulfuric acid
Diagram 3 = Process 2 = hydrolysis of alkyl hydrogen sulfate