Dolbier HW Solutions 378

Dolbier HW Solutions 378 - 472 ENOLS AND ENOLATES 18.6(b...

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472 ENOLS AND ENOLATES 18.6 ( b ) Enolization of the central methylene group can involve either of the two carbonyl groups. 18.7 ( b ) Removal of a proton from 1-phenyl-1,3-butanedione occurs on the methylene group between the carbonyls. The three most stable resonance forms of this anion are ( c ) Deprotonation at C-2 of this b -dicarbonyl compound yields the carbanion shown. The three most stable resonance forms of the anion are: 18.8 Each of the f ve a hydrogens has been replaced by deuterium by base-catalyzed enolization. Only the OCH 3 hydrogens and the hydrogens on the aromatic ring are observed in the 1 H NMR spectrum at d 3.9 ppm and d 6.7 6.9 ppm, respectively. 18.9 a -Chlorination of ( R )- sec -butyl phenyl ketone in acetic acid proceeds via the enol. The enol is achi- ral and yields equal amounts of (
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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