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Acidic Ether cleavage question
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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:
--- Quote ---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?
--- End quote ---
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:
--- Quote ---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.
--- End quote ---
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.
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