Product A and B formed in the following set of reactions are:
Alcohols, Phenols & Ethers · Class 12 · JEE Main Previous Year Question
Product A and B formed in the following set of reactions are:
- a
- b✓
- c
- d
Step 1: Identify the starting material
Methylenecyclohexane = a cyclohexane ring with an exocyclic double bond.
Step 2: Reaction with H+/H2O (acid-catalysed hydration = Markovnikov)
- protonates the exocyclic (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 carbon (boron goes to the less substituted end per steric control).
- After oxidation (), -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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