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Solutions_Manual_for_Organic_Chemistry_6th_Ed 162

Solutions_Manual_for_Organic_Chemistry_6th_Ed 162 - 7-48...

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7-48 CH3 CH3 I I CH -C-C-CH -- -- 3 I I 3 H + HO : 9 o 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 "'9 o H2 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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