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Solutions_Manual_for_Organic_Chemistry_6th_Ed 216

Solutions_Manual_for_Organic_Chemistry_6th_Ed 216 - the...

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9-42 Diols are made by two reactIons fRom Chapter 8 and revisIted in 9±1 (d): either syn-dihydroxylatIon with Os04' or anti±dihydroxyLation vIa an epoxIde using a peroxyacid and water. As thIs probleM says use Inorgan³c reagents, the solutIon sHown here wIll use ´S04µ ¶eca·· the stereochemIcal requirements of syn addIt¸on as outl¸ned IN this ¹olutions ºanual» p¼ 171, Prob·eM 8²35: ½¾¿Àa·kene + syn addition meso ½¾¿ÁalKene + anti add¸tion raceÂc (±) TÃÄÅ¿ÀaÆkEnÇ + syn addition racemÈc (±) TÉÅ¿ÁalKene + anTi addition mes² PaÊt
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Unformatted text preview: the mes² isomer» so syn addItIon wIll have to occur oN the ½¾¿Áa·keNEÌ PAr (b) wiÆl requIre syn addition to the ÍÉÅ¿Àalkene t² g¸ve the (±) productÎ (a) (bÏ ÐCÑCÒÐ ÓCÑCÔ Õa+ alkene must be ½¾¿ to pr²dUce the MEs² pÊoduct from syn addItion» s² Êeduct¸²n is done w¸th Öindlar catalyst to produce the ½¾¿ alkene Õa×Ð2 OS0Ø . ÐCÑCÒÓ ± ÓCÑCÔ ÕaÙ alkene must be TÉÅ¿ to produce the (±) product from syn additIon» so reductIon is done w¸th ÕÚ3 ² OS04 f \ Ð Ð 209 . ÖindLaÊ catalyst Õa . Û3 ÕaÜ2 "! Bf i -c:cJ ×a×Ó2 ±² b f I ±c:cj...
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