Consider the above reaction and identify the product P:
(A)(see structure)
(B)(see structure)✓ Correct
(C)(see structure)
(D)(see structure)
Answer: (B)
Solution
Phosphoric acid protonates the hydroxyl group of cyclohexylmethanol and water leaves, which would give a primary carbocation on the exocyclic carbon. A 1,2-hydride shift from the ring carbon next to it moves the charge into the ring and produces the tertiary 1-methylcyclohexyl cation. Loss of a β-hydrogen from this cation gives the more substituted alkene, so A is 1-methylcyclohexene. Diborane then adds across the double bond with boron going to the less substituted carbon and hydrogen to the more substituted one, and alkaline hydrogen peroxide replaces the boron by a hydroxyl group with retention of configuration at that carbon. The hydroxyl therefore sits on the ring carbon adjacent to the methyl-bearing carbon. P is 2-methylcyclohexan-1-ol.
JEE Main · 2021 · 27 Jul 2021 · Shift 1 · Single correct option