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Unformatted text preview: If no reaction occurs under the indicated conditions, fill both boxes with the symbol X. Br 2 , H 2 O + (a) Br H 3 C CH 3 OH H 3 C HO Br CH 3 (enantiomers) anti addition regioselectivity n/a (b) + HCl Cl (achiral) (c) 1) BH 3 2) H 2 O 2 , NaOH, H 2 O + H CH 3 OH H O H H H CH 3 a racemic mixture arises from syn addition of H and OH non-Markovnikov regioselectivity + (d) 1) O 3 2) H 2 O 2 O O OH (e) + 1) OsO 4 2) NaHSO 3 , H 2 O OH OH (achiral) The fact that dihydroxylation is a stereoselective syn addition does not matter here, since the product does not have any stereoisomers possible!!!...
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- Spring '08