The major product of which of the following reaction is not obtained by rearrangement reaction?
Solution
Solution
Look at the carbocation each reaction goes through.
- (A) 1-Chloropropane with AlCl gives a primary propyl cation, which shifts a hydride to become the secondary isopropyl cation. The product, cumene, comes from rearrangement.
- (B) tert-Butyl alcohol loses water to give the tertiary tert-butyl cation directly. It is already the most stable cation possible, so it simply loses a proton: 2-methylpropene. No rearrangement.
- (C) AlCl/HCl isomerises n-hexane to branched 2-methylpentane by carbocation shifts.
- (D) Neopentyl alcohol would give a primary cation; a methyl shift turns it into a tertiary cation, which loses a proton to give 2-methylbut-2-ene.
Answer: (B).
Answer checked against the official answer key. The solution is our own working.