1、P15 制备稀丙位的卤化物 OAcO NBS/Cl4hv,reflux OAcO BrP17 芳杂环化合物的卤取代 NHMeO Br2/DMF NHMeO BrP34 醚和卤化磷及 DMF 的反应NOMePBr3/DMF6080NBrP41 习题反应产物 H3CHCOH3 P,Br210(CH3)2CHOBrCH3NHCOH3Br,CH3OH50-5CH3NHCOH3BrOHHO NCS,(6H5)3P OHCl反应条件（P37 ）COHAgNO3/KHr.t CO2AgBr2/Cl4heat,1h Br(P40) BrNH21)NaO2,HCl,2O BrF2)HPF6 BrN2PF6(16
2、8)P52 有位阻或螯合酚的烃化 OHOOOH OMeMeI/NaOH OMeOOOH OMeP54 DCC 缩合法NCNHOR NCHNORHHOArH NHCONH+ArORP56 伯胺的制备Gabriel 反应（肼解法）NHOOKOH/EtOHNOOKRX/DMF NOORNH22 OONH+RNH2P62 还原烃化法的应用 NH2CH3ONCHMeH2/Raney Ni NHC2H3P63 Ullmann 反应：芳胺的 N-芳烃化CF3NH2+ClCOHK2CO3/Cu105-10HClp=4F3CNHHO2CP65 芳烃的烃化：Friedel-Crafts 反应R1 +RC AlCl
3、3XR RCRR1HAlCl3X R1CR +AlCl3+HXP79 稀胺的 C-烃化NH+OCH3 NCH3P84 习题反应产物 KNOO+PhOMsHNOODMF NOOPhHNOO PhHNOONH2H2NH2.2OEtO,60+ OOBrOMe SnCl20 OMeO反应条件（P77 ）OOHO OOHORi-Pr2NLi OOLiHORXP85(P77) NCHOOHMeI,NaH,TFNCHOOCH3O 原子上的酰化反应P92 羧酸为酰化剂伯醇酯的制备HOOOHNNHOO+NO2CO2HDEAD/Ph3r.t,1hO2NCO2H2OOHNNHOOP95 活性酯用于大环内脂合成HOO
4、HHHCO2HONSN/Ph3PhH/r.t HOOHHHOP98 酸酐为酰化剂H3CNCH3O 1)(CH32CO)2/Py2)HCl H3CNCH3OCH2C3.l(Anadol)P101 酰氯为酰化剂仲醇的酰化NNNOOHNClClONNCH3.Clpy/CH2l2 NNNOClONNOCH3(Zopiclone)N 原子上的酰化反应P107 酸酐为酰化剂 OOO+PhCH2COHNH2 Tolrefiux,2h NOOCHOH2PhC 原子上的酰化反应P113 Friedel-Crafts 反应（芳烃取代成芳酮 ）S+H3COOCH3H3PO4reflux,2hSOCH3OOO+CH3
5、AlCl390,3h CO2HOCH3NEtO2CCO2Et BF320,15min NEtO2COP116 Vilsmeier-Haack 反应（芳环引入醛基）NHDMF/POCl3CH2l2 H2ONHCHOP122 利用烯胺化进行的 C-酰化反应ONHONO COlEt3N OOH2OClP123 习题反应产物 NBocOH+HNDC/H2Cl2NBocON反应条件 OHC3OClOPhOCPhH3O OHO glycerol OONP124H3COH3CONHCOH3POCl3,toluenH3COH3CONCH3Ac2O,py90-5H3COH3CONCH2COH3P133 Robi
6、nson 环化法OCH3+Obase OCH3CH3AldolOHCH3O-H2OCH3O-羟烷基化（Aldol 缩合）P136 Reformatsky 反应O+BrCF2OC2H5Zn OHCF2OC2H5P138 Grignard 反应O1)BrMg Ph2)H3O OHPh-卤烷基化（Blanc 反应）P139 反应通式+HOH+HCl ZnCl2 Cl+H2O-氨烷基化（Mannich 反应）P143 Pictet-Spengler 反应NHCOCH3NH2 CHONHNHCOCH3NH2OCH3 HCO/HCOH N3CO CH3羰基烯化反应（Wittig 反应）P148 反应机理1
7、48COR3R4(C6H5)3PCR1R2+ (C6H5)3PCR12CR43OCR34R12O(C6H5)3P CR12R43+(C6H5)3POP149 制备环外烯键化合物OCH3CH3Ph3=CH2CH2CH3CH3CH3 CH3P150 制备共轭多烯化合物 CHO+(C6H5)3PCOC2H5COC2H5LiAlH4 CH2OP165 习题反应产物+NO220 NO2C 到 C 重排Wagner-Meerwein 重排 P170 胺与亚硝酸作用生成碳正离子CH3H3H32NH2HNO2 CH3H3H32N-N2 CH3H3H3CH2P171 CH3NH2HO2C NaO2/HOAcHO
8、2C HHH3COPinacol 重排P175 制备环状酮(Tiffenfan 扩环)OHCPhPhH2SO4/Et2Or.t/3h OHCPhPh2 OPhOH0.2molSnCl2/HC(OMe)3-20/5min OH OWoff 重排（-重氮酮生成烯酮）P182ON2hv,CH2l240min/-78/-N2 COhv,O2/CH2l2-78-10/20min OC 到杂重排Beckmann 重排(肟生成取代酰胺)P185 立体专一性 NOH NH2ONOH HNOSchmidt 反应 （叠氮酸）P191 叠氮酸与羧酸生成伯胺HOCCH3CH3COHNa3/H2SO4/CHl3r.t,
9、25h HOCCH3CH3NH2Baeyer-villiger 反应（酮与过氧酸重排成酯）P193 HCOH3PhCO3H/Cl3 HOCH3机理 HCOH3 PhCO3H/Cl3HOCH3HHCOH3 HCOH3OCOPhHOCH3-HCOO2N CH3O3H/AcOHO2NCOO机理 COO2N CH3O3H/AcOHO2NCOH COHO2N O2NCOHOCOH3COHO2N -H-键迁移重排P199 Claisen 重排（烯丙基芳基醚重排为邻烯丙基酚）OCCR heat OHCCR机理OCRC OCHCR OHCCRP200 脂肪族 Claisen 重排Oheat3, OOCO2Et
10、heat3, OCO2EtP202 cope 重排PhPh 150PhPhCH2CH23501h习题反应产物P205 OHHO CH3OH2S4 OP207(P199 烯丙基重排到对位)OCH3CHOO,Tol,215 OCH3CHOO醇类的氧化P220 氯铬酸吡啶鎓盐（PPC）氧化法OOCH2OPC/NaOAcH2Cl2 OOCHOP222 DMSO-DCC 氧化法OHONHOCH3OAc DMSO-DC/H3PO4r.t ONHOCH3OAcOHCP225 1,2-二醇的氧化HOOHPb(OAc)4/TFA(60%) OO醛酮的氧化P226 Dakin 反应OHCHOC6H5COH OHO
11、CH OHOH烯键化合物的氧化P229 不与羰基共轭的烯键的环氧化 t-BuOHMo(C)6 OP232 顺式羟基化O Os4 O HHOHH习题反应条件P248（p218 Collins 试剂 烯丙酮的制备）CH3CrO3.(Py)2 CH3O（P229 过氧酸环烯烃环氧化）OHCH3CH3OH,NaHCO3 OHCH3羰基的还原P263 Clemmensen 反应（酸性锌汞齐还原醛酮为甲基亚甲基）PhCOH2C2OHZn-Hg/Cl/Tolheat CH22CH2OHPhCHPhCOEt Zn-Hg/Clheat PhCH22COEtP264 Wolff-kishner-黄鸣龙还原反应OR
12、 H2NH2 NH2R NaOEtKOHRCH2R +N2P265 腙还原为烃 CO H2NH2 CNH2 t-BuOKDMS CHHP272 Leuckart-Wallach 反应中间体O NCH33HCON(CH3)2 OHN(C3)2HOHCOHOHN(C3)2-H2ON(CH3)2HCOH羧酸及衍生物的还原P278 金属复氢化物的还原CNNO3B2H6/TF25 NO3CH2N2含氮化合物的还原P281 Benoxaprofen 中间体制备O2NHCNH3Fe,NH4Cl95,1.5hH2NHCH3NP282HOO2NNO2Na2S/NH4Cl8085HOH2NNO2习题 反应产物P2
13、90FCHO+NH FHCN FH2CNZnCl2 Zn(BH4)2反应条件P291 COlNO2O2N CHONO2O2NGlymeLiAlHOC(H3)(三叔丁氧基氢化铝锂/甘醇二甲醚)H3CO CN H3CO CHODIBAL-H /2SO4(氢化二异丁基铝/硫酸) OAcO NBS/Cl4hv,refluxOAcO BrNHMeO Br2/DMF NHMeO BrNOMePBr3/DMF6080 NBrH3CHCOHH3C P,Br210(CH3)2CHOBrCH3NHCOH3Br,CH3COH50-5 CH3NHCOH3BrOHHO NCS,(C6H5)3POHClCOHAgNO3/
14、KOHr.t CO2AgBr2/Cl4heat,1h BrBrNH21)NaO2,HCl,H2O BrF2)HPF6 BrN2PF6(168)OHOOOH OMeMeI/NaOHOMeOOOH OMeNCNHOR NCHNORH HOArH NHCONH +ArORNHOOKOH/EtOH NOOKRX/DMF NOORNH2NH2 OONHNH+RNH2NH2CH3CHO NCHMeH2/Raney Ni NHC2CH3CF3NH2+ ClCOHK2CO3/Cu105-10 HClpH=4F3CNHHO2CNH+OCH3 NCH3KNOO+PhOMsHNOODMF NOOPhHNOO PhH
15、NOONH2H2NH2.H2OEtOH,60+ OOBrOMe SnCl20 OOMeOOOHO OOHORi-Pr2NLi OOLiHO RXNCHOOHMeI,NaH,THFNCHOOCH3HOOOHOHNNHOO+NO2CO2HDEAD/Ph3r.t,1h O2N CO2CH2OOHOHNNHOOHOOHHH CO2HOHNSSN/Ph3PhH/r.t HOOHHH OH3CNCH3O 1)(CH3CH2CO)2/Py2)HCl H3CNCH3OCH2CH3.HCl(Anadol)NNNOOHNClClONNCH3.HClpy/CH2Cl2 NNNONClONNO CH3(Zopiclo
16、ne)OOO+PhCH2CHOHNH2 Tolrefiux,2h NOOCHOH2PhS+H3COOOCH3 H3PO4reflux,2h SOCH3OOO+ CH3 AlCl390,3h CO2HOCH3NEtO2CCO2Et BF320,15min NEtO2C ONH DMF/POCl3CH2Cl2 H2ONHCHOO NHO NO COlEt3N OOH2OHClNBocOOH+HN DC/CH2Cl2NBocONOHCH3O ClOPh OCPhCH3O OHOO glycerol OONH3COH3CO NHCOH3POCl3,toluen H3COH3CO NCH3Ac2O,py
17、90-95H3COH3CO NCH2COH3OCH3+Obase OCH3CH3Aldol OHCH3O-H2OCH3OO+BrCF2COC2H5Zn OHCF2CO2H5O1)BrMg Ph2)H3O OHPh+HOH+HCl ZnCl2 Cl+H2ONH COCH3NH2 CHO NHNHCOCH3NH2OCH3 HCO/HCOH NH3CO CH3148COR3R4(C6H5)3PCR1R2+(C6H5)3PCR1R2C4R3OCR3R4CR1R2O(C6H5)3P CCR12R4R3+(C6H5)3POOCH3CH3Ph3P=CH2CH2CH3CH3CH3 CH3CHO+(C6H5)3
18、P COC2H5COC2H5 LiAlH4 CH2OH+NO220 NO2CH3H3H32NH2HNO2 CH3H3H32N-N2 CH3H3H3CH2CH3NH2HO2C NaO2/HOAcHO2C HHH3COOHCPhPhH2SO4/Et2Or.t/3h OHCPhPhH2 OPhPhOHOH0.2molSnCl2/HC(OMe)3-20/5min OH OON2hv,CH2Cl240min/-78/-N2 COhv,O2/CH2Cl2-78-10/20min ONOH N H2O NOH HNOHOCCH3CH3COHNa3/H2SO4/CHl3r.t,25h HOCCH3CH3NH2
19、HCOH3PhCO3H/CHl3 HOCH3HCOH3 PhCO3H/CHl3HOCH3H HCOH3 HCOH3OCOPhHOCOHH3-HCOO2N CH3CO3H/AcOHO2NCOOCOO2N CH3CO3H/AcOHO2NCOOH COHO2N O2N COHOCOH3COOHO2N -HOCCR heat OHCCRO heat3, OOCO2Et heat3, OCO2EtPhPh 150PhPhCH2CH23501hOHHO CH3COHH2SO4 OOCH3CHOO ,Tol,215 OCH3CHOOHOOCH2OHPC/NaOAcCH2Cl2 OOCHOOHONHNOCH3
20、OAc DMSO-DC/H3PO4r.t ONHNOCH3OAcOHCHOOH Pb(OAc)4/TFA(60%) OOOHCHOC6H5COH OHOCH OHOHt-BuOHMo(CO)6 OO Os4 O HHOHOHCH3 CrO3.(Py)2 CH3OOHCH3CH3COH,NaHCO3OHCH3PhCOH2CH2COHZn-Hg/HCl/Tolheat CH2CH2CH2COHPhCHPh COEt Zn-Hg/HClheat PhCH2CH2COEtORR H2NH2 NH2RR NaOEtKOHRCH2R +N2CO H2NH2 CNH2 t-BuOKDMSO CHHONCH3CH3HCON(CH3)2 OHN(CH3)2OHCOH OHNH(CH3)2-H2O N(CH3)2HCOHCNNO3B2H6/THF25 NO3CH2NH2O2N HCNH3 Fe,NH4Cl95,1.5hH2N HCH3NHOO2NNO2Na2S/NH4Cl8085HOH2NNO2F CHO+NH FHCN F H2CNZnCl2 Zn(BH4)2COlNO2O2N CHONO2O2NGlymeLiAlHOC(H3)H3CO CN H3CO CHODIBAL-H /2SO4
