7-48 CH3 CH3 I I CH -C-C-CH ----3 I I 3 H+ HO :9o� CH3 I CH -C-C-CH 3 II I 3 :0: CH3 CH3 CH3 I I CH -C-C-CH 3 I 1+ 3 HO "'9oH2 CH3 CH3 -H20 I�I --I"� CH -C-C-CH 3 I + 3 HO l methyl shift CH3 + I CH -C-C-CH 3 I I 3 : OH CH3 The driving force for this rearrangement is the great stability of the resonance-stabilized, protonated carbonyl group. 7-49 NBS generates bromine which produces bromine radical. Bromine radical abstracts an allylic hydrogen, resulting in a resonance-stabilized aUylic radical. The allylic radical can bond to bromine at either of the two carbons with radical character. See the solution to problem 6-63. NBS c::=>
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