Solutions_Manual_for_Organic_Chemistry_6th_Ed 463

Solutions_Manual_for_Organic_Chemistry_6th_Ed 463 - 19-49...

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19-49 (a) When guanidine is protonaTed, The cation is gReatly sTabilized by Resonance, disT±ibutIng the Positive cHaRge oveR all aToms ²excePT ³´: N ³ 1 2 n ±2 .. II .. w .. Ii . . I. + ± •• H,N-C-NH, h,N±C±NH, h,N² -N³, ³'N= N, ², } ² + ³2µ¶C·¸¹º . »B¼ ½He U¾¿RotonateD molecULe Has a Reso¾ance foRM sHow¾ beLow tHat tHe pÀoto¾aTed molecule Áa¾¾O haveà ½HeReFoReÄ tHe un¿Rotonated forÅ Æs stabilizeD ReLative to tHe pRotonated FoÀmÇ ½his gReateR staBÈÉÈzatÈon of tHe unpRotonated FoÊ Ès ReËecteD in weakeR basÆcÈÌyÍ .. -± + / / . Î2µ µ ´ \ :0: . Ïc¼ A¾Èli¾es aRe weakeR Bases tHan aÐÆpHatÆc amÑnes because tHe eLectRon paiR on the nitRogen is sHaReD wÆtH tHe RÒng, sTaBÈLÆzÓng tHe sysTeÔÕ ½heRe Æs a sTeÖc RequiRement, howeveR× the p oRBÆtal on the µ musØ be paRalleL wÈtH tHe ¿ oRBÆTals on the benzene Ö¾g in oRdeR foR tHe electRons o¾
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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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