Solutions_Manual_for_Organic_Chemistry_6th_Ed 495

Solutions_Manual_for_Organic_Chemistry_6th_Ed 495 - he 3...

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20-43 continued (b) Compound 1 has 8 carBoNs, aNd CompouNd 2 haS 6 ±arbons. Two carBonS have Been lost: the two carbons of the acEtal haVe BeeN cleaveD² (ThiS iS the BeSt way to fIgure oUt reac³Io´S A´D mechaniµM¶· f¸nd out which atoms of the reactant have become which atoms of the prodUc³, ³he´ DeteRmIne wha¹ ºonds have been broken aNd fo»ed²) (c) ¼½e¾aLs a¿À stabLÀ to basÀÁ so the acetal must haVe ºeen cLeaVed when a±Âd was addedà CH3 o A o ÄÅ0+ 5 CÄÅ 4 CÄ2COOH 2 1 ÆÇÈ The carbons haVe been numbered aBoVe to heLp you VÉsuaÊÂze whi±h atoms in the reactant Become wh¸ch atoms in the productË Ìhe oVerall process requires cleaVage of the acetal to expose two aÍcohoÎsÏ
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Unformatted text preview: he 3 aoho at carbon- can Be found n the prodct so it iS the prImaRy alcoho at arBon ha reacts wth the carBoxyic acd to fom the latone 0 RESonAnCE STAbilIzEd; C - LEAvES ThE REACTiOn H + .. OH O . + _ 0 H , 0 . -'- O : O Q O C two faSt . C CH3 . :0 0 C O O O c o ",-h , .. 0 1 C O 490 O + traNSferS . O .q 0 C" O O ! 20 O ' .OQ C H O...
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