A problem I was recently working on poses the following scenario:
A student realizes that protonation of an alcohol makes the -OH into a better leaving group. Therefore, he suggested the following reaction between 1-propanol, sulfuric acid, and trimethylamine. However, this process does not yield the product predicted here. Why not?
The only reason I can think of deals with the leaving group, which I usually only see in tertiary alcohols/SN1 reactions. Therefore, I supppose that since the reaction proceeds via an SN1 mechanism, the carbocation formed in this case (which is primary) would not form at an appreciable rate --> reaction would not proceed to form product predicted.
Is this line of reasoning correct or is there a better reason why the predicted reaction does not occur? Any ideas will be highly appreciated.