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Solutions_Manual_for_Organic_Chemistry_6th_Ed 194

Solutions_Manual_for_Organic_Chemistry_6th_Ed 194 - 8-66 u...

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8-66 u B03 - THF .. H 2 0 2 .. H O - a CH3 111 0 III OH H 8-67 By now, these rearrangements should not be so "unexpected" . � n U " "": H B H 2 0 I Cf. �C H C + H H 3 H (Y C H3 alkyl migration with ring expansion gives carbocation in 6-membered ring--carbocation nirvana! H H H + : !lr: 0 'CH] Br C H 3 You must be asking yourself, "Why didn't the methyl group migrate?" To which you answered by drawmg the carbocation that would have been formed: I;I C+ H O\} -- QC<1' '- CH 3 CH I " H CH3 3 H The new carbocation is indeed 3°, but it is only in a 5-membered ring, not quite as stable as in
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