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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2201

1-Methylcyclohexene is treated with in water and the resulting bromohydrin is then treated with aqueous . The final organic product is

  1. A1-methylcyclohexene
  2. B2-methylcyclohexan-1-one
  3. C1-methyl-7-oxabicyclo[4.1.0]heptane (1-methylcyclohexene oxide)
  4. D1-methylcyclohexane-1,2-diol

Answer: C

The first step gives trans-2-bromo-1-methylcyclohexan-1-ol, with Br on C2 and OH on the tertiary C1. Base forms the alkoxide, which displaces the adjacent anti bromide by intramolecular SN2. The product is the epoxide.
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