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Osmium tetroxide is commonly employed as a reagent for

1. adding hydroxyl groups to acetylenes
2. converting olefins into cis-diols
3. converting olefins into trans-diols
4. hydroxylating carbonyl compounds

Correct answer: converting olefins into cis-diols

Solution

Osmium tetroxide adds across a C=C double bond via a cyclic osmate ester, delivering both -OH groups to the same face. Hydrolysis gives a cis (syn) 1,2-diol from the olefin.

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