Acid-Catalyzed Cleavage of Tert-Butyl Cyclohexyl Ether Mechanism
What is the mechanism for the acid-catalyzed cleavage of tert-butyl cyclohexyl ether with trifluoroacetic acid?
How does the reaction yield cyclohexanol and 2-methylpropene?
Answer:
The acid-catalyzed cleavage of tert-butyl cyclohexyl ether with trifluoroacetic acid proceeds through several steps to yield cyclohexanol and 2-methylpropene.
Firstly, in the presence of trifluoroacetic acid, the ether undergoes protonation to form a more reactive intermediate. This protonated intermediate then undergoes cleavage of the C-O bond, resulting in the formation of a carbocation intermediate and an alcohol molecule. The carbocation intermediate, being unstable, quickly undergoes deprotonation to give 2-methylpropene and a cyclohexanol molecule.
The overall reaction can be summarized as follows:
tert-butyl cyclohexyl ether + trifluoroacetic acid → cyclohexanol + 2-methylpropene