Sunday, November 19, 2017

organic chemistry - Possible nonclassical ion from a bicyclic system


In this question a bicycling alcohol is reacted with acid to make what appears to be a tertiary carbocation, and the OP asked whether it could become aromatic. The given answer suggests it could be, but only if a nonclassical ion is formed. So, does that happen?


The substrate is 8a-methyl-1,3,4,8a-tetrahydronaphthalen-4a(2⁠H)-ol.



Answer



I don't think it is necessary to consider a mechanism with a nonclassical carbocation. It would undergo normal rearrangement with a 1,2-methide shift within the same ring. See the mechanism I posted in previous question you were directing to:



Rearrangement to Aromatic


Answer to this question would support for my mechanism.


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