Conc me chanism o o h o h n br o h br

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Unformatted text preview: conc. conc. Me chanism ? :O : + :O H :: :O H : : N Br : : :O + H+ :Br :− : :N O: : Br : + N Br : :: + :B r :− : : : :: O: : :O : :O H : N: : :O :: S toichiom try: Br2 doe not show up, but is theactual brom e s inating spe s! cie doe : + Br Br: P r oton sh if t (ta utom e ri sm ; Se ct ion 1 3-7 ) AllylicF11 AllylicF11 :: :N : :O H Prope ge rate a sym e ne ne s sym trical allylic radical and only one m one product. For unsym e m m ixture . Ratios de nd s Ratios pe unsym trical syste s: m on %radical characte on e carbon and TS le r ach s ading to products. B. S 1: TheAllylic C ation is S tabilize d B. N 2 + CC C C HH H H + CC C C HH H H C C C HC H H HC l -H lO C H+ C C C H OH H H HC CC HC H HC H OH +H Two products C S 2: Fast! Theallylic TSis stabilize and theallylic carbon . N2: d TS is re lative e ctrophilic. ly le re TSde localize d ‡ sp = e -withdrawing 2 C l .. .. . . - δ δ C C C HC H H HC l 100 tim s faste than e r + NaI CC C C HH H I - Cl δ C C C HI H H HC +C l - D. Allylic Organom tallics e D. CH 3...
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This note was uploaded on 09/04/2010 for the course CHEM 10966 taught by Professor Vollhardt during the Spring '10 term at Berkeley.

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