Solutions_Manual_for_Organic_Chemistry_6th_Ed 362

Solutions_Manual_for_Organic_Chemistry_6th_Ed 362 - 1 6-36...

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Unformatted text preview: 1 6-36 continued propagation HE r + n! � r-·CH2 + B r - Br (c) Both reactions are S N2 o n primary carbons , but the one at the benzylic carbon occurs faster. In the transition state of S N2, a s the nuc leophi le is approaching the carbon and the leaving group is departmg, the electron density resembles that of a p orbital . As such, it can be stabi lized through overlap with the 1'[ 8s ystem of the benzene ring. : Br : •• 6 1.& resonance-stabilized ----l� .. B r· + H 1 6-37 (a) � stabi li zation through overl ap 8- :O-CH3 •• VlCH� + 3 i somers only 1 isomer ( c ) The original compound had to h ave been meta-dibromobenzene as this is the onl y dibromo isomer that gives three mononitrated products . Br Br Br � VlBr � �N02 o Vl y + Br Br ...
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