Does acid-catalyzed alkoxyation have the same mechanism as acid-catalyzed hydration?

Question

Nolan Allen · Accepted Answer

Not always. Their mechanisms are generally similar. The general steps are: The main difference is that the alcohol can be any type (primary, secondary, tertiary, very sterically hindered, not very sterically hindered, etc), whereas obviously water is pretty much always water (unless you deuterate it or something and it's #D_2O#, but that isn't extremely significant here).  This difference allows for the alkoxylation reaction to be not necessarily an #S_(N)2# reaction. If the alcohol is bulky (like tert-butyl alcohol), it could easily be an #E1# or #E2# reaction.

Christian Anderson · Answer

undefined No, acid-catalyzed alkoxylation and acid-catalyzed hydration do not have the same mechanism. In acid-catalyzed alkoxylation, an alcohol reacts with an alkene in the presence of an acid catalyst to form an ether. In contrast, in acid-catalyzed hydration, an alkene reacts with water in the presence of an acid catalyst to form an alcohol. The mechanisms involve different steps and intermediates, although both reactions proceed via carbocation intermediates in the presence of an acid catalyst.