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1、关于含氮有机化合物(4)现在学习的是第1页，共70页CH3CH2NO2NO2CH3RNO2RONO现在学习的是第2页，共70页CH3ONO+-12-12NO0.137 nmNO0.122 nmRNOORNOO+现在学习的是第3页，共70页RONOCH3(CH2)4Br+AgNO2CH3(CH2)4NO2+CH3(CH2)4ONO7580%14%现在学习的是第4页，共70页RNO2HRNH2HNO2HNOHNHOHNH2现在学习的是第5页，共70页RCHNOORCHNOHORCHNOHONaOH现在学习的是第6页，共70页3HCHO +CH3NO2 OHHOCH2CCH2OHNO2CH2OH现在
2、学习的是第7页，共70页RCH2NO2HONORCNOHNO2+H2OR2CHNO2HONOR2CNO2NO+H2OR3CNO2HONO现在学习的是第8页，共70页NClOONHOOO现在学习的是第9页，共70页 RNH2R2NHR3N R4N+X-季铵盐R4N+OH-季铵碱NH3NH4+X-铵盐NH4OH现在学习的是第10页，共70页 CH2NHCH3CH2NH2 CH3CH2CHCH2CH2CH2CH3 CH3CH2CHCHNHCH3NHCH2CH3CH3H3C现在学习的是第11页，共70页 (CH3)2CH4N+I-N+CH3 OH-CH2CH2OHCH3CH3 现在学习的是第12页，共
3、70页NHH3CHsp3112.9o105.9o现在学习的是第13页，共70页CH3N+H5C2CH2CH=CH2phCH3N+C2H5CH2=CHCH2phNR1NR1R2R3R3R2现在学习的是第14页，共70页 RNH2 +H2O RNH3+OH-RNH2 +HXRNH3+X-OH-RNH2现在学习的是第15页，共70页CH3NH2 (CH3)2NH (CH3)3N NH3 NH2 3.38 3.27 4.21 4.76 9.37 NNH2CH3NH2O2N13.0 8.92现在学习的是第16页，共70页CH3N+CH3CH3HOH2CH3N+HHHOH2OH2OH2CH3N+CH3HH
4、OH2OH2现在学习的是第17页，共70页RXR4N+X-NH3RXSN2RNH2RXR2NHRXR3N现在学习的是第18页，共70页RCNR2 +HClORCNHR +HClORCNH2 +HClORCCl +RNH2ONH3R2NH氢氧化钠氢氧化钠或吡啶或吡啶RCCl +R3NORCCl +RNH2O现在学习的是第19页，共70页RNH2R2NHR3NSO2ClSO2NHRSO2NR2不反应（不溶于NaOH水溶液）NaOHSO2NRNa+-RNH2R2NHR3NSO2ClSO2NHRSO2NR2不反应（不溶于NaOH水溶液）NaOHSO2NRNa+-RNH2R2NHR3NSO2ClSO2N
5、HRSO2NR2不反应（不溶于NaOH水溶液）NaOHSO2NRNa+-RNH2R2NHR3NSO2ClSO2NHRSO2NR2不反应（不溶于NaOH水溶液）NaOHSO2NRNa+-RNH2R2NHR3NSO2ClSO2NHRSO2NR2不反应（不溶于NaOH水溶液）NaOHSO2NRNa+-RNH2R2NHR3NSO2ClSO2NHRSO2NR2不反应（不溶于NaOH水溶液）NaOHSO2NRNa+-现在学习的是第20页，共70页CH3CH2CH2+Cl-+N2醇、烯、卤代烃等 CH3CH2CH2NH2NaNO2HCl1o胺CH3CH2CH2N+NCl-重氮盐NH2 +NaNO2 +HCl
6、O5oCN2+Cl-现在学习的是第21页，共70页Ar(R)NH(或R2NH)+HONO2o胺致癌剂致癌剂3o胺N(CH3)2+HONOR3N+HNO2R3NH+NO2-Ar(R)NNO(或R2NNO)N-亚硝基胺ONN(CH3)2(绿色结晶)现在学习的是第22页，共70页NH2+3Br2H2ONH2BrBrBr+3HBrNH2(CH3CO)2ONHCOCH3Br2无水CH3COOHNHCOCH3BrNH2BrH+or OH-现在学习的是第23页，共70页NH2浓浓H2SO4N+H3OSO3H1802000CH2ONHSO3H重重排排NH2SO3H现在学习的是第24页，共70页CH2N+(CH
7、3)3Cl-C12H25N+(CH3)3Cl-R3N +RIR3N+R I-CH2Cl +(CH3)3N现在学习的是第25页，共70页R4N+X-+Ag2OH2O(CH3)3N+CH3OHR4N+OH-+AgXN+CH3CH3CH3CH3OH-1301350C现在学习的是第26页，共70页CH3CH2CHCHCH2H+N(CH3)3HOH-+2N(CH3)3+H2O55.7%1.3%2CH3CH2CH2CH=CH2+CH3CH2CH=CHCH3现在学习的是第27页，共70页CH3CH2CHCH CH2HN(CH3)3 HOHCH3CH2CH2CH=CH2 +N(CH3)3 +H2O+-CH3C
8、H2CHCHCH2H+N(CH3)3HOH-现在学习的是第28页，共70页3)CH3CH2CH2N(CH3)2+CH2CH2+H2O3)CH3CHCH2+(CH3)3N+H2OCH3CH2CH2N+CH2CH3OH-CH3CH3CH3CH2CH2N+(CH3)3OH-CH3CH2CH2NHCH2CH31)2CH3I2)Ag2O,H2OCH3CH2CH2N(CH3)21)CH3I2)Ag2O,H2O现在学习的是第29页，共70页?试试2次彻底甲基化2次Hofmann消除NHCH3现在学习的是第30页，共70页 NH3RXSN2RNH2RXRXRXR2NHR3NR4N+X-CH3ClKNH2/NH
9、3(l)CH3NH2CH3NH2+68%32%现在学习的是第31页，共70页CH3ClCl-_CH3CH3NH2CH3NH2+NH2-68%32%现在学习的是第32页，共70页 NOHNa,C2H5OHor LiAlH4NH2 现在学习的是第33页，共70页COH2/Ni+NH3CHNH2C OH2/Ni+RNH2CHNHRC OH2/Ni+R2NHCHNR2+NH3RCH2CHORCHCHNH2烯烯胺胺RCH2CHNH亚胺H2/NiRCH2CH2NH2现在学习的是第34页，共70页KOHN-OOKOHH2ORNH2 +COO-COO-OOONH3NHOO1oRXSN2NROO现在学习的是第3
10、5页，共70页 RCNH2OBr2,NaOH H2ORNH2现在学习的是第36页，共70页 NH2 O5oCN2+Cl-+NaCl +H2ONaNO2+HCl现在学习的是第37页，共70页NN:+NN:ArOHNNArOH+-碱OOHNNAr碱芳基重氮酸芳基重氮酸现在学习的是第38页，共70页N2+HSO4H+H2O+H2OOH2+N2+N2OH +N2-H+OH现在学习的是第39页，共70页N+NX-CuXHClN+NX-CuCNKCN碘代物的制备碘代物的制备X+N2（X=Cl、Br）CN +N2IN+NCl-KI现在学习的是第40页，共70页CuBrHBrClBr讨论讨论HNO3H2SO4
11、NO2NO2ClNaNO2HBrN2+Br-ClFeCl3Cl2HClFeNH2ClBrCl现在学习的是第41页，共70页+N2N2+Cl-H3PO2H2O+N2N2+HSO4-CH3CH2OH现在学习的是第42页，共70页 NN+NN+N2+Cl-+OHNaOHH2ONNOH现在学习的是第43页，共70页N2+Cl-+N(CH3)2CH3COOHH2O NNN(CH3)2现在学习的是第44页，共70页NNO-Na+NR2H+OHH+OH2+NHR2+N2+Cl-NaOHNNOHNaOH现在学习的是第45页，共70页N2+Cl-+NH2CH3COONaCH3COOH,200CNNNHPhNH3
12、+Cl-PhNH230450CNNNH2现在学习的是第46页，共70页C H2NNCH2NNCH2NNCH2NN现在学习的是第47页，共70页 RCOOCH3 +N2RCOOH +CH2N2-N2R C O O C H3OCH3OHCH2N2RCOOH +CH2N N RCOO +CH3N N现在学习的是第48页，共70页ArndtEistert ReactionAg2OH2ORCH2COOHCORClCORCHN22CH2N2CORCH2Cl+N2CH2N2现在学习的是第49页，共70页OCCHRWolff重排CORCHNNCl H-Cl-CORCHNNHCH2NNAg2OH2ORCH2CO
13、OHCORCl +CH2NN CORCHNN_CORCH现在学习的是第50页，共70页 (Molecular Rearrangements）Nucleophilic Rearrangement 现在学习的是第51页，共70页CCZLCCZ L-H+CCZ+12重重排排CCZ+Nu-H+CCZNuCCZ现在学习的是第52页，共70页Pinacolic RearrangementCH3CCH3OHCCH3CH3OHH+H2OCH3CCH3OHCCH3CH3OH2+CH3CCH3OHCCH3CH3+CH3CCH3CCH3CH3OH+CH3CCH3OCCH3CH3CH3CCH3OHCCH3CH3+H+
14、现在学习的是第53页，共70页CCR2R1R3R4OHOHH+COHCH2OHPhPh+CCH2OHPhPhPh2CHCHO+CCHOHPhPhHH+-现在学习的是第54页，共70页PhCOHCPhOHCH3CH3H+PhCCPhOHCH3CH3+Ph2CHCOCH3CH3H+Ph2C COH+H3C CH3现在学习的是第55页，共70页CH3OClCH2=CH R3CR2CH CH3H现在学习的是第56页，共70页CCR2R1R3R4OH+CCR2R1R3R4OH+CCR2R1R3R4OHNH2HNO2N2CCR2R1R3R4OH+现在学习的是第57页，共70页 Wagner-Meerwei
15、n rearrangementH+CH3CCH3CH3CH2OHH2OCH3CCH3CH3CH2OH2CH3CCH3CH3CH2H+Cl-CH3CCH3CH2CH3现在学习的是第58页，共70页 Beckmann RearrangementCRRNOHH+CRRNHOCRRNOH2H2O+_CRRN+CRRNH2OH2O+CRRNHO_H+现在学习的是第59页，共70页CCH3PhNHO RCNH2OBr2,NaOH H2ORNH2PCl5CPhCH3NOH现在学习的是第60页，共70页CCZ+12重重排排CCZ+12CCZL L-Nu-CCZNuEt2OCCH3CNHOC2H5HCH2C2H
16、5H2SO4CH3CONHCC2H5HCH2C2H5现在学习的是第61页，共70页OHCH3OHCH3H2SO4OCH3CH3CH3OHOHCH3H2SO4CH3CH3O现在学习的是第62页，共70页CH3OHOHCH3H2SO4CH3CH3O123456123456123456OHOHCH3CH3现在学习的是第63页，共70页 CH3C PhOCF3CO3HCH3C OPhO现在学习的是第64页，共70页CF3COOHOCH3C PhOH+CH3C PhOHCF3COOHOCH3CPhOHCF3C O OOH+CH3COPhOH+CF3COOHH+CH3C OPhO现在学习的是第65页，共70页CF3CO3HCH2Cl2CH3C C(CH3)3OPh C CH2CH3OCH2Cl2CF3CO3H现在学习的是第66页，共70页 CCZL L+CCZ12重重排排CCZ-现在学习的是第67页，共70页Ph CCH3CH3CH2CHO(t C4H9O)2Ph CCH3CH3CH2COPh CCH3CH3CH2H rearrangementCCH3CH3CH2PhH HCCH3CH3CH2PhCOPh CCH3CH3CH3现在学习的是第68页，共70页 NHNHH+H2NNH2现在学习的是第69页，共70页感谢大家观看感谢大家观看现在学习的是第70页，共70页