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JEE Main levelSingle correct optionDifficulty 2 of 3o3194

Which of the following halohydrins gives cyclohexene oxide readily when treated with aqueous NaOH?

  1. Atrans-4-chlorocyclohexan-1-ol
  2. Bcis-2-chlorocyclohexan-1-ol
  3. Ctrans-3-chlorocyclohexan-1-ol
  4. Dtrans-2-chlorocyclohexan-1-ol

Answer: D

The alkoxide formed by NaOH must attack the carbon bearing Cl from the back side, so O and Cl must be anti (diaxial in the chair). This is possible in the trans-2-chloro isomer. In the cis isomer the groups are always gauche and no anti arrangement is possible. The 3- and 4-chloro isomers would give strained bridged ethers.
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