Solutions_Manual_for_Organic_Chemistry_6th_Ed 264

Solutions_Manual_for_Organic_Chemistry_6th_Ed 264 - I 1-62...

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Unformatted text preview: I 1-62 o ( a) c ntinued H ( b) T herem ust be a stere che cal require ent in this eli nation I f theS a z eff alkene is not p rod o mi m mi . yt uced because them eth l gr up is trans o thel eaving grou then the H an the leaving gr upm ust be trans and yo t p, d o the e mi nationm ust be anti the characte stic stereoche ist o f E2 elim nati n This evidence li ri m ry i o. differentiates between the two p ssibilities inp a t (a). o r 11-63 � H3� POCI3 H3CK:;> NOTH3C �H h�h H H OH H • G5J� N) H •• CI '0 •• E2 • O( H H + 0 +1 H N + I CP=O O-C 1 1 l p yrid ine .....- Z aitsev ( a) I t is equall likel for pr o nation to occur first on the ringo x gen fol o wed b ri ng opening, h en y y ot y,l y t replacemento f b water y . D r K ant rows i suggests this alte ative H e and I will ar wrestle o determ ne wh ch me han . o k rn . m t i i c ism is c rrec o _ 2 H..V H H2� H00 ·9t H OCH3 � ('l H .. �-� H H+kO � 0 O ---.- + · U�HQCH3CH30..H � uRCH3H 1 Qtc5� } H 2� � O:OH H+ O:OH --0OH H20 r; H f) 9.) H H ° ° 1+ H HO .. :0 1 + -H -- H •• --- + • • '--- � •• H .. \ •• ° • • •• '---"" H •• + •• ' t .. ° H � ��+ ' O � H 257 H0 ° H ...
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