第10章取代酸.ppt

OHCOOHOC OHCHCH3OH取代酸取代酸羟基酸羟基酸羰基酸羰基酸醇酸醇酸酚酸酚酸CH3OC CH2COOH卤代酸卤代酸氨基酸氨基酸CH2-C-OHOClCH2-C-OHONH2OHCH3 CH COOH 3 2 12-羟基丙酸羟基丙酸CH2 COOHHO CH COOHHO CH COOHHO CH COOH HOC COOHCH2 COOHCH2 COOH酒石酸酒石酸柠檬酸柠檬酸2-羟基丁二酸羟基丁二酸2,3-二羟基丁二酸二羟基丁二酸1234苹果酸苹果酸2-羟基羟基-1,2,3-丙烷三羧酸丙烷三羧酸123 CH3CH2COOHCH2CH2COOHOHCH3CHCOOHOH：H3CHCOHCOOHAg(NH3)2NO3H3CCCOOHORCHCOOHOH稀H2SO4RCHOHCOOH+R CHHOCOHORCHOHCHOOR CHOCORCHOCO交酯RHCOHH2C COOHRHCHC COOH+H2OH2CH2C OHCH2COOHH2CH2CCH2COOH3CHCOHCOOH H2CHCHOCOOHCOOH OHCOOHOHCOOCH3OCOCH3COOHCOOHOH(CH3CO)2OCOOHOCOCH3乙酰水杨酸乙酰水杨酸COOHOHCH3OHCOOCH3OH水杨酸甲酯水杨酸甲酯COOHOHOH COOHOHHOOHC CH2COOHOCH3COH丙醛酸（3-氧代丙酸或3-羰基丙酸或甲酰乙酸）COOH丙酮酸CH3COCOOHCH23-丁酮酸（乙酰乙酸或3-氧代丁酸或3-羰基丁酸CHOCOOH浓NaOHCannizzaro反应COOHCOOHCOOHCH2OH+H3CHCOHCOOHOH3CCOCOOHCHOHCHOHCOOHCOOHH2O-CHCCOOHCOOHOHCH2CCOOHCOOHOCO2CH3CCOOHO酒石酸草酰乙酸烯醇式草酰乙酸丙酮酸-H3CC COOHOH2SO4稀CH3CHO+CO2H3CC COOHOH2SO4CH3COOH+浓或COCO2H3C C COOHOCH3COOH+Fe2+O+H2O2 CH3-C-CH2-COOHOCH3C CH2COOHO+CO2OCH3C CH3C CH2COOHO+CO2ROC CH3RH3CC CH2COOCH2CH3O CH3COOC2H5H-CH2COOEtEtONaCH3COCH2COOEtEtOH+CH3COCH2COC2H5OCH3CCHCOC2H5OOH酮式（92.5%）烯醇式（7.5%）CH3COCH3CH3CCH2OH0.00025%CH3CCHCOOHOC2H5CH3COCH2COC2H5OCH3CCHCOC2H5OOH酮式（92.5%）烯醇式（7.5%）CH3C-CH2-COC2H5OO或稀或稀OH-,H+浓浓OH-CH3CCH3OCH3C-OH +其余O稀稀H+CH3C-CH2-COC2H5OORONaCH3C-CH-COC2H5OONa+CH3C-CH-COC2H5OOR RC+-X-OR+-X-CH3C-CH-COC2H5OOCROCH3C-CH-COC2H5OOCRO稀OH-浓OH-酮式分解酸式分解CH3C-CH-COC2H5OOR稀OH-浓OH-酮式分解酸式分解CH3CCH2ROCH3CCH2CROORCCH2COHOORCH2COHO酮酮-二酮二酮-酮酸酮酸酸酸COCH3例一：H3C COCH2COOEt1.EtONa2.卤代2.Br(CH2)3Br1.EtONaH3C COC COOEtH2CCH2CH2稀OH-H3C COCHCH2H2CCH2CH3COCHC2H5CH3CH3COCH2COOC2H5CH3COCHC2H5CH3C2H5ONaCH3COCHCOOC2H5Na+-CH3COCHCOOC2H5C2H5-I+-C2H5C2H5ONaCH3COCCOOC2H5C2H5Na+-CH3COCCOOC2H5CH3-I+-C2H5CH3稀OH-COOHEtOOCCH2EtOOCEtONaCH2(CH2Br)2-NaBrH2CCH2H2CCCOOEtCOOEtCH2CH2CH2CH(COOEt)2BrEtONa-NaBrLiAlH4CH2OHCH2OHP，Br2CH2BrCH2BrNaCH(COOEt)2-NaBrH2CCH2CCOOEtCOOEt-CO2水解TM-NaBrEtONa