有机化学课件：第十二章羧酸

1、R COOHR COXR COOCORR COORRCNR CONH2R CONHRR CONR2RCHCOOHXRCHCH2COOHOHRCHCOOHNH2BrCH2CH2CH2COOHCH3CHCHCH2CH2COOHHOCCH2CHCH2CH2CHCH2COHOOCH2CH3CH3HOOCCOOHCOOHCOOHCH3COOHHHCOOHCHCOOHOHCH2COOHCH2COOHCOHOH125 111 124 COCH3CH2CH2CH3O2, 醋醋酸酸钴钴951.015.47MPaCH3COOH + HCOOH + CH2CH2COOH+ CO + CO2 +酯酯和和酮酮(57%)

2、(12%)(23%)(17%)(22%)CH3+ 3/2 O2钴钴盐盐或或锰锰盐盐COOH+ H2O165,0.88MPa,(92%)CO + NaOH2100.8 MPaHCOONaH2SO4HCOOHCH3CH2CHO + 1/2 O2(CH3CH2COO)2 Mn0.1 MPa,CH3CH2COOH(90%)CH3OH + CORhC I2,1502000.51.0MPaCH3COOH(90%99%)(CH3)3CCHCH2OHC(CH3)3K2Cr2O7 - H2SO4(CH3)3CCHCOOHC(CH3)382%CH3CNH2O, H2SO485%CH3COOH(CH3)3CMgCl

3、+ OCOOCO MgClC(CH3)3H3O+(CH3)3CCOOHBrMg乙乙醚醚MgBrCO2H3O+COOHOK+ CO2180 2502.02 MPaOHCOOKH3O+OHCOOHONa+ CO21500.5MPaOHCOONaH3O+90%OHCOOHCH3(CH2)4CCH3CH3(CH2)4COOHOI2/NaOHRCOOHH OHOHHRCOO HH OCROCOCOROHCCCOOHCOOHAr 1710 cm-11715 1690 cm-1 1700 1680 cm-1COOHCHRRCOOH + NaOHRCOO Na + H2ORCOOH + NaHCO3RCOO

4、Na + CO2 + H2ORCOONa + HClRCOOH + NaClC CH RNH2 RHOHCH3CH3CH3COOH,HCOOH0.120 nm0.134 nmHCOORCOOHOHROR+ H+COCORCOORCOORCOO1212C COOHClClClC COOHClClHC COOHClHHC COOHHHHCClClClCCHCH2CCRCH3CH2CH COOHCl CH3CH2CHCOOHCl CH2CH2CH2COOHClHOOCCH2COOHpKa1 = 2.9HOOCCH2COO+ H+HOOCCH2COOpKa2 = 5.7 OOCCH2COO+ H+HO

5、2CCO2H HO2CCH2CO2H HO2C(CH2)5CO2H OOCCH2COOHXCCCOHOCOOHO HOHCOOHCOOHCOOHHO.R C OHOPX3R C XO(Ar)(Ar)(Ar)(Ar)R C XOR C XO+H3PO3+POX3+SO2+HXRX5SOCl2蒸出蒸出2 RCO2H CH3COCCH3O OCOROCOR + 2CH3COOHCCOOOHOH230CCOOO+ H2OCOO Na + CH3CH2 COClCH3O CH3COCH2CH3+ NaClCOCH3COOH + HOC2H5H+CH3COC2H5O+ H2OCH3COOH + CH3(C

6、H2)3OH树树脂脂C SO3H,CaSO4(干燥剂)室室温温，1 10 00 0CH3COO(CH2)3CH3 + H2OCH3COO+CH2ClCH3COCH2O+ ClOHC6H5+ CH318OHCOC6H518OCH3+ H2OCOO HRH+O HRO HRCO HCOCO HROHOHROHRCOHCOHOHROH2ROR-H2OCOHRORCOHOHROHRCOH-H+COORRCOHRORRCOOH + HOCR3RCOOCR3COOH+NH2COO H3N190CONH+ H2OCH3OCH3OCO2HLiAlH4H2OCH3OCH3OCH2OH(93%)RC O+NH3R

7、C ORC NH2H2OOOONH4H+H2ORCOOHRCOOHH2/ZnNa/ROH；RCOOHNaBH4/H2O/OH或NaBH4/C2H5OHCH2=CHCH2COOHLiAlH4/醚H2O/H+CH2=CHCH2CH2OH12醚O2NCOOHB2H6/ H2OO2NCH2OH12R C XO79%Cl3CCOOHCHCl3 + CO2COOHO2NNO2NO2O2NNO2NO22 CH3(CH2)12COONa电电解解CH3(CH2)24CH3NO2CNCOCl,H2N (CH2)3CH H2N (CH2)3CH2NH2NH2HCOOCO2鸟胺酸腐肉胺H2N (CH2)4CH H2N

8、 (CH2)4CH2NH2NH2HCOOCO2赖氨酸尸胺OCH3C CH2 CH3CCH3+CO2OCOOHCH2CH2COOHCOOH300CH2CH2CCOOO+ H2OHOOCCH3COOH+CO2CH2 COOHHOOC CH2 COOH+H2O( )3CH2CH2CH2COOOC乙酐P2O5或HOOCCOOHHCOOH + CO2CH2CH2COOHCH2CH2COOHBa(OH)2CH2CH2CH2CH2C O + CO2 + H2O(CH3)2CHCH2CH2COOHBr2, PCl3(CH3)2CHCH2CHCOOHBrRCH2CH2COOHBr2100。CRCH2CHCOOHBrBr2P/P+RC CHCOOH NaOHC2H5OH/RCH CHCOONaH+HBr2RCH CHCOOH NaOHH2O/RCH2CHCOONaH+RCH2CHCOOH2NH3RCH2CHCOONH3+NH4BrKCNRCH2CHCOOKCNH2ORCH2CHCOOHCOOH=OHOH2P + 3X22 PX33 RCH2COOHPX33 RCH2COX + H