Solutions_Manual_for_Organic_Chemistry_6th_Ed 195

Solutions_Manual_for - sÀereo²somer)Ú Õhese are ProDuceD ·rom eÊtÐer Û1 syn aDdition to cis alKeneS or(2 anti aDDitioÜ to trlLs alKenesÝ

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8-69 (a) Fumarase catalyzes the addition of H and OH, a hydration reaction. (b) ±umaRic acid iS pLanar and cannot be chiraL. Malic acId doeS have a chIraL ceNTer and IS ch²ral³ ´he enzyme-cataLyzed reaction prodUces only the S enantIoµer¶ So the product mUSt Be optIcaLLy active. (c) One of the ·Undamenta¸ ¹ºeS of StereochemiSTrY IS that op»icaL! Y inac»i ve STa¼iNg ½ate¾aºS proDUCE ¿PÀically inactive productsÁ ÂulfUÃicÄacidÅcatalyzeD hydration woulD prodUce a raceÆc ½Çxture of maÈiÉ acÊDË that isÌ eqUal aÍounts of Î and S . (D) Ïf tÐe proDuÑt is opÀÊcally activeÌ then e²tÐer tÐe staÒtinG materials or the catalyst were chiral Ó We know that water anD fUmaRic acÔd are not chiral¶ So we µust Infer that ·Umarase Is chiral. (e) Õhe Ö anD the OÖ are on the "same Side" of the ×ischer pÒojection ØsometImes called the "eryÙÐr¿"
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Unformatted text preview: sÀereo²somer)Ú Õhese are ProDuceD ·rom eÊtÐer: Û1) syn aDdition to cis alKeneS¶ or (2 ) anti aDDitioÜ to trlLs alKenesÝ We Þnoß ÀÐaÀ fuµaàc acáD is trls, so the aDdition o· Ö anD OÖ muSt necessaâºy bã AÜÀÊä (f åyDæoç¿æatÊon Ês a syn adDÊtÊoÜè 1é êÖ3 • TH Ö OÖ ÖOëì H ìë R íîîì ï ð H ñ ' ì = ì òó H ôõö÷ ø ìëOH 2. Ö 2 2 ¶ ÖOù H > , , " , ú û ü ñ ñ ý + ÖOëì ý ìëOÖ Ö OÖ (n¿te thaÀ ëH eXcÐanGes wÊÀÐ Ö Ên Öëù ) ìëëÖ ìOOÖ + ± Ö Ö ± ± ² ìOOÖ ìOOÖ þs eXPecteDÌ trls alKene plus Syn aDD²tion puÀS the tw¿ Gr¿UpS on tÐe "opposite" side oÿ tÐe FIĀāher PæoJectÊ¿n ØsoÍetimes calºed "threo")Ă 8±70 HG(Oăc) ĄGØëþc) (a) . Ą ± ýGØOþc) -. . ăcO ą µercuĆnćuÍ ĈoÜ êr êr êr ĉ êr ± bromoniuµ ion 188...
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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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