JEE Main · 2024 · Shift-IIhardALCO-023

Product A and B formed in the following set of reactions are:

Alcohols, Phenols & Ethers · Class 12 · JEE Main Previous Year Question

Question

Product A and B formed in the following set of reactions are: image

Options
  1. a

    image

  2. b

    image

  3. c

    image

  4. d

    image

Correct Answerb

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Detailed Solution

Step 1: Identify the starting material

Methylenecyclohexane = a cyclohexane ring with an exocyclic \ce=CH2\ce{=CH2} double bond.

Step 2: Reaction with H+/H2O (acid-catalysed hydration = Markovnikov)

  • \ceH+\ce{H+} protonates the exocyclic \ce=CH2\ce{=CH2} (less substituted end) → generates a tertiary carbocation on the ring carbon.
  • Water attacks the tertiary carbocation → 1-methylcyclohexanol (tertiary alcohol).
  • A = 1-methylcyclohexanol

Step 3: Reaction with BH3, then H2O2/NaOH (hydroboration-oxidation = anti-Markovnikov)

  • BH3 adds to the less hindered terminal \ce=CH2\ce{=CH2} carbon (boron goes to the less substituted end per steric control).
  • After oxidation (\ceH2O2/NaOH\ce{H2O2/NaOH}), -OH replaces the boron at the terminal carbon.
  • Product: cyclohexylmethanol (1-(hydroxymethyl)cyclohexane), a primary alcohol.
  • B = cyclohexanemethanol (cyclohexylmethanol) ✓

Step 4: Key contrasting principle

Both reactions work on the same substrate but give completely different products:

  • H+/H2O = Markovnikov → OH on more substituted C → tertiary alcohol.
  • BH3/H2O2 = anti-Markovnikov → OH on less substituted C → primary alcohol.

Key Points to Remember:

  • Exocyclic double bond in methylenecyclohexane: more substituted carbon is the ring carbon.
  • Markovnikov addition: OH at tertiary (ring) carbon → 1-methylcyclohexanol.
  • Anti-Markovnikov (BH3): OH at exo-methylene (CH2) → cyclohexylmethanol (primary).

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Product A and B formed in the following set of reactions are: (JEE Main 2024) | Canvas Classes