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Why in the cis-alkene reaction both methyl groups are represented by two wedges

ID: 593585 • Letter: W

Question

Why in the cis-alkene reaction both methyl groups are represented by two wedges and the H are represented by two hatches why in trans-alkene CH3 and H are alternatively in the form of wedges and hatches? I think that the priority should remain the same C-C HO OH identical; a mesO compoun OsO (2S,3R)-2,3-Butanediol ROOH CH HO OH cis-2-Butene (achiral) C-C H C CH3 (2R,35)-2,3-Butanediol CH HO OH a pair of (2S,35)-2,3-Butanedienantiomers ROOH a racemic H3C mixture HO trans-2-Butene (achiral) C-C H,C (2R,3R)-2,3-Butanediol

Explanation / Answer

Answer: When it react with OsO4, the dihydroxylation occurs in syn fashion only. Therefore, both the hydroxyl groups in the product will be in same side and preserving the original stereochemistry of substituents in alkene. The H and Me groups can be represented by either dashed or wedged arrow. However, interchanging will only generate another identical meso compounds.

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