Whether water is added to a reaction synthesizing these compounds determines if they were made in Woodward or Prévost (“PRAY-voast”) conditions. In one reaction, the reagents DHQ (“D-H-Q”) and DHQD (“D-H-Q-D”) act as chiral auxiliaries used to selectively form two different forms of these compounds. NMO (“N-M-O”) acts as a stoichiometric (“stoy-KEY-oh-meh-trick”) oxidant in another reaction used to synthesize a racemic (“rah-SEE-mick”) mixture of these compounds named for the Upjohn company. That non-oxyamination reaction used to form these compounds, which utilizes (*) osmium tetroxide as a catalyst, is named for K. Barry Sharpless. Vicinal (“viss-sin-all”) examples of these compounds include ethylene glycol, which can be synthesized by treating ethene with a peroxyacid. Under acidic conditions, epoxides open up to form these compounds. For 10 points, name these compounds containing two hydroxyl groups. ■END■
ANSWER: diols [accept trans diols; accept anti diols; accept vicinal diols; accept dihydroxyls; accept glycols before “ethylene glycol” is read; prompt on alcohols; prompt on hydroxyls until “hydroxyl” is read]
<Kane Nguyen, Chemistry>
= Average correct buzz position