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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc125

Hex-3-yne is converted into hexane-3,4-diol by the sequences below. Which sequence(s) give the meso diol?

  1. A, Lindlar catalyst; then cold dilute alkaline
  2. BNa / liquid ; then a peracid, followed by
  3. C, Lindlar catalyst; then a peracid, followed by
  4. DNa / liquid ; then cold dilute alkaline

Answer: A, B

Lindlar gives the Z alkene and Na/NH3 gives the E alkene. Syn dihydroxylation of Z gives meso, and syn dihydroxylation of E gives the racemate. Epoxidation then acid opening is overall anti: anti addition to E gives meso, and to Z gives the racemate. So Z + syn and E + anti give meso.
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