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Question

Consider the following reactions
Meso−butan−2,3−diol is formed in:

246997_980dbadd9bfa410a81e23ba36e4c6f41.png

A
(I),(II),(V)
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B
(III),(IV),(VI)
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C
(I),(II),(IV)
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D
(III),(IV),(V)
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Solution

The correct option is A (I),(II),(V)
Mesobutan2,3diol is formed in (I) KMnO4, (II) OsO4/NaHSO3 and (V) H2O2+OsO4. The addition is syn addition. Two OH groups are added across carbon carbon double bond from the same side. Mesobutan2,3diol has plane of symmetry.

In the cases (III) HCO3H/H2O, (IV) MMPP+C2H5/H2O and (VI) H2O2+SeO2, trans addition results in (±)-butan-2,3-diol . Two OH groups are added across carbon carbon double bond from the opposite sides.

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