The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. What is the mechanism by which this ether forms?
The ether forms by an
The overall reaction is
The substrate is a 3° halide, and the ethanol is both a weak nucleophile and a polar protic solvent, so the reaction will go by an
There will be no rearrangements, because the carbocation is already 3°.
Step 1. Loss of
Step 2. Nucleophilic attack by ethanol
Step 3. Deprotonation of the oxonium ion