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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro214

An alkene A on treatment with mCPBA followed by dilute aqueous acid gives a meso diol, while the same alkene with followed by gives a racemic diol. A is

  1. Acis-but-2-ene
  2. Bbut-1-ene
  3. Ctrans-but-2-ene
  4. D2-methylpropene

Answer: C

mCPBA/H3O+ results in net anti addition of two OH groups, and OsO4 in syn addition. For trans-but-2-ene anti addition gives the meso diol and syn addition gives the racemic pair. For cis-but-2-ene the outcomes are reversed, and but-1-ene or 2-methylpropene cannot give a meso diol.
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