JEE Main · 2021 · 27 Jul 2021 · Shift 1 · Alcohols Phenols and Ethers

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Consider the above reaction and identify the product P:
  1. (A)(see structure)
  2. (B)(see structure)
    ✓ Correct
  3. (C)(see structure)
  4. (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 -hydride shift from the ring carbon next to it moves the charge into the ring and produces the tertiary -methylcyclohexyl cation. Loss of a -hydrogen from this cation gives the more substituted alkene, so A is -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 -methylcyclohexan--ol.

JEE Main · 2021 · 27 Jul 2021 · Shift 1 · Single correct option

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