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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1229

The ketone shown is treated with methylmagnesium bromide and then aqueous acid. The product is then heated with concentrated sulphuric acid. Which structure is the major final organic product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

Cyclohexanone adds the methyl group to give 1-methylcyclohexan-1-ol. Acid-catalysed dehydration of this tertiary alcohol proceeds by E1 through the tertiary cation and follows Zaitsev's rule, giving the more substituted endocyclic alkene 1-methylcyclohexene.
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