How do I recognize an SN1 reaction and how do I formulate the corresponding mechanism?
Hello,
I don't quite understand this problem :/ How do I know that 2-methyl-2-propanol (tert-butanol) reacts with dilute hydrochloric acid to produce this product? I know this is a typical SN1 reaction. But I don't quite understand how I can reliably identify an SN1 reaction and formulate its mechanism.
It's really important that I understand this mechanism, as it's highly relevant to my exam, but unfortunately, I don't have a clear grasp of it yet. I would be very grateful if someone could help me 🙂
(1 rating, 1 votes, rated)You need to be a registered member to rate this.
Loading...
In acidic conditions, it is difficult to formulate a mechanism involving hydroxide ions. In this case, the reaction proceeds according to SN1 because the intermediate carbenium ion is stabilized quite well by the inductive effects (+I effect) of the three methyl groups. Mechanistically, the first step involves the protonation of the hydroxy function to tert-but-OH2⁺. In the second step, a water molecule is split off, leaving the tert-butyl⁺ with the charge on the tertiary C. In the next step, the chloride ion Cl⁻ attacks there nucleophilically, and the whole process is complete.