Solutions_Manual_for_Organic_Chemistry_6th_Ed 205

Solutions_Manual_for_Organic_Chemistry_6th_Ed 205 - 9 - 19...

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Unformatted text preview: 9 - 19 CH3- r =c + CH3-C ==C - CH2CH3 H ! 1 H2 : O ) CH2CII3 ;)(� ( both 2° vinyl carbocations CH3- + = H2 : 0 A -CH2CH3 CH3- 'f 'f H ! 1 �H :OH 1+ I) CH3-C == C-CH2CH3 1 +1 HO: H H ! I) ( H2 : O H2 : 0 ) :H R -CH2CH3 CH3- H: � 'f 'f H+ ) ! -CH2CH3 H + resonance1 CH3 - C - C-CH2CH3 CH3-C-C-CH2CH3 stabilized carbocations , '",\ r' 1 H :O-H H t H+ + H t (resonance forms not shown) H CH3-C-C-CH2CH3 t I I Hi .. � ; : H-O : H �. 0 t H2 : H II 0 3 -pentanone H CH3-C-C-CH2 CH 3 I II 1 0H 2 -pentanone The role of the mercury catalyst is not shown in thi s mechanism. As a Lewis acid, it may a ct l ike the proton in the first step, helping to form vinyl cations; the mercury is replaced when acid is added. -H + ---I.... CH3-C ==C - CH2CH3 +Hg I OH I 198 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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