Solutions_Manual_for_Organic_Chemistry_6th_Ed 249

Solutions_Manual_for_Organic_Chemistry_6th_Ed 249 - 1 1-2 8...

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Unformatted text preview: 1 1-2 8 c ntinued o (b) oH.f H+ oH H2 O<0H .O.H cYf G:O-H CX;; �C � /\ ���; +OH o H2··: /�-H a a0a � H 1+ - ° � 30 and doubly benzylic carbocation •• \ + Ph Ph P h P h Ph � � Ph U Ph non Si .--- - + Ph Ph Ph Ph Ph 11 2 9 - � � S imil r o the pin c l re rr ngement, thi mech ni m at ao a a s as inv lve a c rb c ti n next o a na lc h l, with o s a oao t oo re rr ngement o a p r o n ted c rb ny l . Relie of aa t ot a ao f so meri n s tr in in the cycl pr pa ne s a na dded ga oo i a dv nt geof h e re rr n gement. aa t aa 11 -30 () a OH0 H+ V- C OH H , /H �C-C-H C==C H HH H • f'-.-- / + / " / 1 1 rng I e x n o•n pa s i O-H [c � CH + H 1 / •• � - 3 ( c) 11 -3 1 ( a) (c ) Cl-C-CH2CH2CH3 + HOCH2CHzCH3 (b) CH3(CH2hOH Cl-CCH2CH3 0CH3C-<, }-OH + CI-CCH(CH3h [>-OH Cl- 0 + H3C",C'H +H� if II ° 2 ( b) ° ° c:fCH] 0 CH2=0 (Y"' + � HS�4- [�-CH3 H C 1 +O-H ij� ( d) ° II ° II 242 �: ° ° II ( d) + II � !J ...
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