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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 fi 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
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