[mranderson]

Can somebody explain to me why this reaction would form an alcohol rather than alkyl halide. I predicted that the ether oxygen would be protonated and then able to leave to form a carbocation (SN1), but if that were the case, why would the chloride attack the methanol carbon rather than the carbocation intermediate?

[Orcio_87]

I predicted that the ether oxygen would be protonated and then able to leave to form a carbocation (SN1), but if that were the case, why would the chloride attack the methanol carbon rather than the carbocation intermediate?

Maybe chloride doesn't attack anything (methanol), but acts more like a catalyst.

After all - concentration of HCl is not given, and molar concentration of H₂O is bigger even in conc. HCl.

[Orcio_87]

Maybe chloride doesn't attack anything (methanol), but acts more like a catalyst.Maybe chloride doesn't attack anything (methanol), but acts more like a catalyst.

It should be "maybe the chloride doesn't attack anything, but HCl acts more like a catalyst" (sorry for the typo).

[wildfyr]

Bingo. Water is the nucleophile.