Solutions_Manual_for_Organic_Chemistry_6th_Ed 312

Solutions_Manual_for - Begin by transforming the alcohols into good leaving groups like halides or tosylates NaSH N aOH PBr3'S N a'SH Br OH 1 4-17

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14-±7 Begin by traNsformIng The alcohols Into good LeavIng groupS ±Ike Ha²Ides or tosyLates: PBr3 ³a´µ /.± ²³´ ³aO¶ ²³´ /.± - · Br µ .±²³ ´µ¶· ' ´ ¹º a + »SC¼ O»½ 1 A ¾ d ¿ À a pyÁ Me I  à 14-18 »He SUlfUr at tHe center of ÄuStard GaS ÅS aN exÆelLent NUcLeopHILe, aNd cHlorIde IS a deceNt LeavÇÈG groUp. ´ULfur caN do IN interal nucleopHILÅÆ SUÉSItUtÅoN to ÄaKe a reactIve SUlFonIUÄ Salt aNd tÊe ËULÌÍr eqUÅvaLent of aN epoxÅdeÎ (a) CL Ï •• Ð Cl C '- . S . verY reaÆtÅve aLKylatING aGeNt Ñ Ò ´ Ó ÔÕ INactÅvated eNzyÖe (b) ³aOCÕ IS a powerfUl oXÅdÅzING aGeÈt× Øt oxIdÅzeS SuLFUr to a SUlfoxIde or Äore ²ÙkelY a SULfoNe, eÅtHer of wÊÅÆÊ ÅS No LoNGer nUc²eopÊÅlÅc, preveNtÅNG foRÖatÅoÈ of tÊe cyclÅc ½U²foNÙuÄ saLtÚ
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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