Solutions_Manual_for_Organic_Chemistry_6th_Ed 495

Solutions_Manual_for_Organic_Chemistry_6th_Ed 495 - Ìhe...

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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: Ìhe 3° aʱohoÊ at carbon-Ð can Be found ¸n the prodÑctÒ so it iS the prImaRy alcohoÓ at ±arBonÔÕ ÖhaÖ reacts w¸th the carBoxyÍic ac¸d to fo×m the la±toneØ Ù 0 ÚÛ RESonAnCE STAbilIzEd; ÄÅC - LEAvES ThE REACTiOn H + .. ÜOH OÄ ± . + _ Ù 0 H ,± • Ü0 •. -'-² OÝÄ ³ : Þ O Q OßÄ CÄÅ two faSt Äà . C Ýá CH3 . ± :0 ·0 · ± • CÄÅ OÄ ÜOÝÄ ´ ÄÝ O Ü c o ",-h , .. Ä ²0 ±²³´ 1µ¶ CÄÅ Oâ 490 · Oã Û+ traNSferS ² . ÜOÚÄ .q ä0 ¸ Câå" OÄ Oâ ! æ Ä20 ÜOçÛ ' Ù .OQ · ¹º C • ²H Oâ ³...
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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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