Dolbier HW Solutions 366

Dolbier HW Solutions 366 - 460 ALDEHYDES AND KETONES:...

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Wolff Kishner reduction (N 2 H 4 , KOH, ethylene glycol, heat) converts the aldehyde group to a methyl group in step 4. The synthesis is completed in step 5 by hydrolysis (H 3 O 1 ) of the acetal- protecting group. 17.42 We need to assess the extent of resonance donation to the carbonyl group by the p electrons of the aromatic rings. Such resonance for benzaldehyde may be written as Electron-releasing groups such as methoxy at positions ortho and para to the aldehyde function increase the single-bond character of the aldehyde by stabilizing the dipolar resonance forms and increasing their contribution to the overall electron distribution in the molecule. Electron- withdrawing groups such as nitro decrease this single-bond character. The aldehyde with the low- est carbonyl stretching frequency is 2,4,6-trimethoxybenzaldehyde; the one with the highest is
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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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