Dolbier HW Solutions 340

Dolbier HW Solutions 340 - 434 ALDEHYDES AND KETONES:...

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17.16 Ylides are prepared by the reaction of an alkyl halide with triphenylphosphine, followed by treat- ment with strong base. 2-Bromobutane is the alkyl halide needed in this case. 17.17 The overall reaction is In the f rst step, the peroxy acid adds to the carbonyl group of the ketone to form a peroxy monoester of a gem -diol. The intermediate then undergoes rearrangement. Alkyl group migration occurs at the same time as cleavage of the O @ O bond of the peroxy ester. In general, the more substituted group migrates. 17.18 The formation of a carboxylic acid from Baeyer Villiger oxidation of an aldehyde requires hydrogen migration. C 6 H 5 COOH O O CH O 2 N m -Nitrobenzaldehyde O COH O 2 N m -Nitrobenzoic acid OH CH O OCC 6 H
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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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