(10)C-NNHCalts (11)No Reaction (2CH CH3 -o -a OH OH CHsCH3 。-CH,(克莱门森还原)()-CH,(黄鸣龙还原) CHBr (COOH.CH O-am0Ow⊙8a OH 14-3 (1)CH:CHCH2CHO (2)CH3CH2CH2CH2OH Br (3)CHCH=CHCHO (CH3CH=CHCH2OH CH3(CH2)2CH2OH (s)CH3CH2CH2CHO (CH3CHCHCHO Br Br (CHCH-CHCH OH CH3CHCH2CHO CN CN 日CH,CH-CHCHSO,Na OH CH3CHCH2CHO SO3Na (9)CH3COOH CO2 (CHCH-CHCH-CHCH-CHCHO ()CHO (Diels-Alder) CCH3 9C2H5 CHCH-CHCH OC.Hs2 CH3 CH3 O C=NNHC6H5 (10) (11) No Reaction (12) O C CH3CH3 CH3 OH OH OH CH C C (13 ) (14 ) CH3 OH CH (15 ) C2H5 (16 )
 ￾✂✁  C2H5
 Br O CCH2 C NO2 CH3
18 COOH O (19 ) + CHI3 (20) (21 ) C CH2 C OH CH3 O 14-3 Br (1) CH3CHCH2CHO (2) CH3CH2CH2CH2OH (3 ) CH3CH=CHCHO (4 ) CH3CH=CHCH2OH + CH3 (CH2 )2CH2OH OH (5 ) CH3CH2CH2CHO (6 ) CH3CHCHCHO Br Br CN (7 ) CH3CH=CHCH + CH3CHCH2CHO CN (8 ) CH3CH=CHCH SO3Na OH (9 ) CH3COOH + CO2 CH3CHCH2CHO SO3Na CHO CH3 (10) CH3CH=CHCH=CHCH=CHCHO (11) (Diels-Alder) OC2H5 (12 ) CH3CH=CHCH OC2H5