Solutions_Manual_for_Organic_Chemistry_6th_Ed 482

Solutions_Manual_for_Organic_Chemistry_6th_Ed 482 - 20-13...

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Unformatted text preview: 20-13 For the sake of space in this problem, resonance forms will not be drawn, but remember that they are critical! '0' '0' Ph 0 ).? plus resonance forms Ph �H H�CH 3 H O .... Ph10 H + ;» H .... "CH 3 H� CH 3 H • • • XJ �+ ....H+ ·H � + + Ph 5 Ph � OH H� CH 3 H O .... P h1 OH ..0+ .. ;» H ·'CH 3 H� CH 3 + ·0 .... H • • • + H� ·0 .... H ).? plus 6 resonance forms + X=' '!J + � t+ c: h Ph o H+ . H ...0..... H H 'CH 3 +H + + ,- 0h-t-OH H+ � . H ... 0..... H + 'CH 3 (+ •• Ph / c '" H p lus resonance forms O'CH 3 , HERE'S THE DIFFEREN CE! C ANNOT LOSE H+ TO HR CH 3+ MAKE CARBON YL H "'" C H 3 �O Ph H O'CH 3 H� CH 3 ..... CH 3 o p Ph 'CH 3 + -H20 Ph +OH ,o o 4 Ph �H o + II � O"'" C H 3 Ph yO� plus 5 resonance forms .\ CAN LOSE H+ 'C � MAKECARBONYL +H� CH 3 TO o 'CH 3 t -H20 'CH 3 4 77 ...
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