1559T_ch17-304-32211/3/0510:48Page314 EQA 314.Chapter 17 ALDEHYDES AND KETONES:THE CARBONYL GROUP CH-CH2 38.(a)H.HCHCHou 09 CH.CCH.CH.CHOH CC CH.CH2 60 OH (b)Co Hso.3-pentanoneC product CHCH:OH (e)cC..5-pentanedial product,via H HO OH (d).HCH.CH.o 0 1.Mg.THF Br 2.CH.c product 39. CH.CH.CH.CH 盖”脸 =394nn Bottle 2 40.(a)HaNNH2,H2O.HO,A(Wolff-Kishner reduction of both carbonyl groups) (b)H2.Pd-C,CH,CHOH(Selective reduction of alkene) 38. (a) (b) (c) (d) 39. Extended conjugation would be expected to shift the absorptions of these hydrazones to longer wavelength, just as it does with the parent ketones. So, 40. (a) H2NNH2, H2O, HO,  (Wolff-Kishner reduction of both carbonyl groups) (b) H2, Pd-C, CH3CH2OH (Selective reduction of alkene) CH3CH2CH2CH O Hydrazone max 358 nm (yellow) Bottle 2 CH3 C H C H CH O Hydrazone max 377 nm (orange) Bottle 1 C H C H CH O Hydrazone max 394 nm (red) Bottle 3 O Br O 1. Mg, THF O 2. CH3CH O OH O H
, H2O product 1. BH3, THF 2. H2O2, OH H 3. PBr3
, HOCH2CH2OH O O H2O O O H H etc. H H O HO OH 2PCC, CH2Cl2 H2O 1,5-pentanedial product, via H
, C6H5NH2 CH3CH2OH CrO3, H2O, H2SO4 3-pentanone product CH3 product CH3 OH 1. H
, H2O 2. LiAlH4 O O CH2CH2 CH3CCH2CH2CH2C 2. Mg, THF 1. PBr3 3. CH3CCH3 O O O CH2CH2 CH3CCH2CH2CH2OH H
, HOCH2CH2OH 314 • Chapter 17 ALDEHYDES AND KETONES: THE CARBONYL GROUP 1559T_ch17_304-322 11/3/05 10:48 Page 314