Solutions_Manual_for_Organic_Chemistry_6th_Ed 328

Solutions_Manual_for_Organic_Chemistry_6th_Ed 328 - 1 5 - 7...

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Unformatted text preview: 1 5 - 7 con / (c) � H ..... H &{ I � n Br - Br Br H 2C - H ?? + a llylic ..... Br H2C - H .. :Br : Br H 2C - C - C == CH2 H H W hile the bromonium ion mechanism i s typical for isolated alkenes, the greater stabi lity of the resonance­ stabilized carbocation w i l l make it the lower energy intermediate for conj ugated systems. (d) C� A g+ a llylic H3C - C == C - CH2 H I H I- II (f r } Ii � ) II O II ! I II I II .. AgCl H3C - C == C - CH2 H H + I II I Br H � + I )} -? ? == CH2 + H H Br H 2C - C == C - CH2 H H IIII - : B�: _ t wo carbons are e lectron deficient so nucleoph i le can attack either Br � � - H3 CH2 H20. . + H- �H •• .. • H2O . H3C - C == C - CH2 H ? H + H 3C - C - C - CH2 H H v? •• + - H _ t wo carbons are e lectron defic ient so nucleophile c an attack either H2 9. H 20 .. OH H 3C - C == C - CH2 H H + OH H 3C - C - C == CH2 H H 3 21 ...
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