Solutions_Manual_for_Organic_Chemistry_6th_Ed 401

Solutions_Manual_for_Organic_Chemistry_6th_Ed 401 - bY...

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17-60 (a) This is an example of knetic versus thermodynamIc control of a reaction. At low temperature, ±He knetic proDuct predomInates: ²n tHis case³ almost a ´ : ´ mIxture of oRtHo and paraµ ¶·ese two ¸sOMers Mus± be fO¹eD at apprOXimateLy equaL rates at º» C¼ At ´00» C½ however³ enough energy is prov¾deD FOr tHe desulfonation to Occur rapiDly; the Large excess of the para isomer inDicates the para is more stabLe, eVeN though it is formed initially at tHe Same rate as the ortho. (b) THe proDuct from tHe 0¿ C reac±iOn wiLL equiLibrate as ¾t is waÀeD, anÁ at ´00» C wiÂl prOÁuÃe ÄHe saÅE rat¾O of proÆucts as the reaction which was ruÇ ini±iaLLY È00» CÉ È7Ê6È 6 Br2 ËeBr3 Q q Ì Ii Íg CÎÏCCÎ2CÎÏ Î+ ² ³ eÐher Br ÑgBr CÎÏ ÒC ÒCÓÔCÎÏ I (pOss¾bLe aL±eÕa±¾ve sÖntHeses ¾ncLuÁe
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Unformatted text preview: bY GgarD) 76 reacVe ses + frOm ch OrO bezene + a a 50C s We saw N CHapter 6, the carbOns O he cener riNg of aNHracene re suscepble to elecrOpHLi atON LeavNg twO sOLateD benzene rngs O tHe eNs ezNe s sucH a reactve ienopHLe t He reluctant anhracene is forced into a ieLs-Aler reacOn 7-6 CL a (a J -C a C CC2C a C 1 CL w ;H C C CL Cl 4-T L a , :C Cl Cl-+ C C C TwO nuceophLc aomatc substutios fOrm a new sxmembere rng (hough no sHOW here, tHis reacto wouLd fOLlow tHe standarD aDDiton-elimInation mechanism) 395 (TI I E compound UED to po I on UainiAn PolITIcL leDEr, BoRs YushChEnko.)...
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