材料科学与化学工程学院2.1.2烯烃的官能团化CH3CHCH2BrCH2CHCH2-H·´Ó¦£¨O)OHCCHCH2Ñõ»¯Ç×µç¼Ó³ÉHXX=Cl,Br,HSO4CH3CHCH3X+Y+Br2,HOClCH2CHCH3×ÔÓÉ»ù¼Ó³ÉCH3CH2CH2Br´ß»¯¼ÓÇâCH3CH2CH3¿¨±öHCCH2H3CCH2KMnO4Ï¡¡¢ÀäHCCH2H3COHOHORCO3H(1)O3(2)Zn/H2OCH3CHOHCHO+KMnO4Ũ¡¢ÈÈCH3COOHHCOOH+(1)B2H6(2)H2O2/OH-CH3CH2CH2OHXXYÂíÊϹæÔòλÖÃÑ¡ÔñÐÔÁ¢Ì廯ѧ材料科学与化学工程学院2.1.4芳烃的官能团化2.1.4.1芳环上的亲电取代反应RClAlCl3X2FeX3RCX2CHX2AlCl3HClZn-HgSO3/H2SO4HNO3H2SO4XRRCOClCORCH2RSO3HNO2X2(Cl,Br)FeOHNaOHArN2+Cl-OH-材料科学与化学工程学院OBr2OBrCH3COONO2OHNO2HCH3COObaseONO2C5H5N,SO3OSO3H(CH3CO2)O/BF3OCOCH3dioxane/0°CBr2-50°COHNO2HCH3COOOOOOOOOOHHHHOOO+呋喃的亲电取代、加成反应内式（90％）外式材料科学与化学工程学院SBr2CH3COONO2SClSNO2SCH3COOHSBrCl236%SClCl14%SClCl13%ClClH2SO4SSO3HH3PO4(CH3CO2)OCOCH3HCHOHClSCH2ClROOCCCCOORSCOORCOORCOORCOOR噻吩的亲电取代、加成反应材料科学与化学工程学院2.1.5.2六元杂环化合物Br2HNO3/H2SO4°C300NaNH2N亲电取代°C330H2SO4°C350NBrNNO2NSO3H亲核取代PhLiNNH2NPhNOHNHOKOH材料科学与化学工程学院SO3RXNNO2NNNOCOCH3NNO+_PCl3RCO3HPCl3Cl(CH3CO)2ONSO3+_HNO3/H2SO4+O_PCl3CHCl3NO2NRX+_高温重排NHX+_RNHX+_R+材料科学与化学工程学院SOCl2RCOCl,(RCO)2O(RCO)2OO_Lewis酸HOH»òH+HX+HOOHOCOR(RCO)2SO2HOR或RX,OHCCHO2+ArOHHH或RCOCl,R3NArOCORArOR_(RCO)2SO2或RX,OHCH2N2ArOCH32.2官能团的转换2.2.1羟基的转换材料科学与化学工程学院2.2.3醛、酮的的转换R'OH/H+NaHSO3HCNH2O(1)R'MgX(1)XCH2COOEt/ZnPh3PCOCH2RR(H)COHOR'RCH2(R)HR'OH/H+COR'OR'RCH2(R)HCOHSO3NaRCH2(R)HCOHCNRCH2(R)HCOHCOOHRCH2(R)HH2O(2)H2OCOHR'RCH2(R)HNH2-YCNCH2RR(H)YY=OH,NH2,NHPh,NHCONH2,etc.CR'2CCR'2CH2RR(H)OH-RCH2COH(R)HCHRCO(R)HRCH2C(R)HCRCO(R)HHCHO/(CH3)2NHHClCOCHRR(H)CH2N(CH3)2(2)H2OCCH2COOEtOHRCH2(R)HCCHCOOEtRCH2(R)HH2OR'CHCOOEtXRONaOR'COOEtRCH2(R)HCOHHRCH2(R)HH2/NiorLiAlH4Zn-Hg/HClCHHRCH2(R)H材料科学与化学工程学院2.2.4羧酸及其衍生物的转换NH3R'OH/H+H2O/OHNH3,X2/NaOHRCH2OHLiAlH4RCOOR'RCONH2Br2/PRCOOH_H2O/H+,orOH_PCl5orPCl3orSOCl2RCOX(RCO)2ORCOONaArHAlX3RCOArLiAlH4P2O5/H2ORCNRCH2NH2RNH2R'HCCOOHBr材料科学与化学工程学院RCOOR"LiAlH4orNa/C2H5OHRCOCHCOR"RCH2OHArCOR(2)H2OH2RCOOR'R'OHR"CH2COR"RCH2OH(1)2R"MgXR'CR'OHRCOXR'OH+RCR"R"OHR"OH/H+orRONa+R'OHEtONaR"R"CH2COOR'EtONaRCOCHCOOR'R"ArHAlX3Pd-BaSO4RCHO(1)LiAlH4(2)H3O+RCOR'R'MgXEt2O/LowTRR'MgXEt2O/RT材料科学与化学工程学院2.2.5硝基的转换ArNHOHNa2Cr2O7ArN2ArNO2ArNH2CF3CO3HH2SO5+Zn,NaOH/CH3OHArNH2NH4ClZnZn,NaOH°H2SO40CArNOArNNArArNHNHArFe/HClorN2/NiZn,NaOHHNO3As2O3NaOHArNNArO_材料科学与化学工程学院2.2.6氰基的转换R'OH/HHH2O+R(1)R'MgX(2)H2ORCH2NH2RCONH2RCOR'RCOOR'H2/NiorLiAlH4_CNorOH+
