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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1089

Cyclohexanone is subjected to (i) , dry ether; (ii) ; (iii) conc. , heat. The major final product is

  1. A1-methylcyclohexene
  2. Bmethylcyclohexane
  3. C1-methylcyclohexan-1-ol
  4. Dmethylenecyclohexane

Answer: A

Step (i)-(ii) gives the tertiary alcohol 1-methylcyclohexan-1-ol. Acid-catalysed dehydration proceeds through the tertiary carbocation, and the more substituted (trisubstituted) alkene is the major product by Zaitsev's rule: 1-methylcyclohexene.
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