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1第一章卤化反应1，写出下列反应的主要产物（或试剂）①CH3OC6H4CHCHHBr2CCl42~5℃C6H4OH3CHHBrHBr②OH3CCH3OOCH3CH3BrBrOOCCl4ref5fOH3CCH3Br③C8H17I2,CF3COOAgC8H17O2CF3CI④THF00OBrMeNBSOSiMe3Me⑤2HOHHI(C6H5)3PI2C6H6ref⑥OAcOOBrBrBrBrOEt2O,HCL⑦ICH2COOMeAgFFCH2COOMe⑧OAcCOCH3CHOH2Odiox,100COCBrBr,NaOHHOCOOHHClH2O⑨3B2H6BH2CHCH3CHCH3BH3CCH3HI2NaOCH3CH3OHCH3CH2CHICH32,写出下列反应可能产物①(CH3)3CCH2OHHBr100℃封管(CH3)2CCHCH3+(CH3)2CHCH3CH3+(CH3)3CCH2Br②CH3CCCOOCH3CH3NBS,(C6H5CO)2O2CCl4refHCBrH2CCCOOCH3CH3HCH3CCCOOCH3CH2BrH③CH3CCH2CH2CH3OBr2KClO3,H2O40~45℃CH3COCH2CH2CH3CH2COCH2CH2CH3BrBr④CHCC2H5HCHCH3CCH3Cl2,CH3COOH25℃ClClC2H5CHCH3COCOCH3ClC2H5CHCH3CClOCOCH3C2H5HHH++3，写出下列反应的主要试剂及条件①C(CH2OH)4PBr3/170~180℃C(CH2Br)4②HOOC(CH2)4COOHSOCl2/RefClCO(CH2)4COCl③PhCH2COCH3SOCl2/Refor,Cl2/加热PhCHCOCH3Cl④4OCOOHOorI2/LTA/CCl4/refHgO/I2/加热orAgNO3KOHI2加热第二章烃化反应4，完成下列反应①COOCH3OHOHCH3INaOHCOOCH3OCH3OH②OHOCH3OHMe2SO4K2CO3OCH3OCH3OH③H3CH2COCH2CH3OH,H2SO4CH3OH,CH3ONaH3CH2COCH3CH2OHH3CH2COHCH2OH5④(H2C)5CNHOMe2SO4(H2C)5CNCH3O⑤NO2ClO2NPhNH295℃NO2NHPhO2N⑥HOHH3CC6H4SO2OHCH3C6H4SO2Cl(EtO2C)2HCHCH2(COOC2H5)2C2H5ONaC2H5OH⑦NH2CH2OHRaney-Ni,加热NHCH2⑧OH3CLDA/CH3OCH2CH2OCH3-40~0℃OLiH3C62,完成下列反应过程①OCCONCH(COOC2H5)2OCCONC(COOC2H5)2NaC2H5ONaC2H5OHClCH2COOC2H5150~160℃OCCONC(COOC2H5)2CH2COOC2H5HClH2OCH3COOHH2NCHCOOHCH2COOH②CHO+CH3NH2H2/Raney-NiCH2NHCH3OCH2NCH3CH2CH2OH③C6H5CH2NH2(C2H5O)2PHOC6H5CH2NHP(OC2H5)2OH2CCHCH2Br/50%NaOH(n-C4Hg)4NHSO4C6H5CH2NP(OC2H5)2OCH2CHCH2C6H5CH2NHClCH2CHCH2HCl④7OCH3(H3C)3CNH2C6H6ref带水NCH3(H3C)3CC2H5MgBrOrefNCH3(H3C)3CMgBrH2COrefCCH2ClCH3OCH3(H3C)3CCH2C=CH2CH3第三章酰化反应①H3COOCH3OCH3+CH3COClAlCl3H3COOCH3OCH3CCH3O②CCCH2OHO2NHOHNHCOCHCl2H+CH3(CH2)16COClN/C6H6CCCH2OOC(CH2)16CH3O2NHOHNHCOCHCl2H③8ClCH2CONHSCCOOHNOCH3+H2NNSNNNNCH3OH2CSDCCTHFNNSNNNNCH3OH2CSClCH2CONHSCNOCH3OC④CH3CH3(CH2)5COClAlCl3ClCH2CH2ClCH3CH3O⑤OCH3H3COH3COH3COZn(CN)2/HCl①DMF/POCl3②H2OOCH3H3COH3COH3COCHO⑥+C6H5NCHOCH3ACONaH2OPOCl390~95℃CHO⑦9CH3COCH2COOC2H5+HO140℃4~5小时H3CCOCH2COO2，完成下列合成路线①OHEt2SO4,NaOH或C2H5X,NaOHOC2H5DMFPOCl3OC2H5CHOCl2OC2H5COClNSOH2NCH3CH3COONaNSONHCH3CH3COONaOC2H5OC②以苯和丁二酸为起始原料合成四氢萘+OOOAlCl3CH2CH2COOHOZn-HgHClCH2CH2CHOOHHFCH3H2OOZnHgHCl10第四章缩合①COCH3+HCHO+CH3NHCOCH2CH2NCH3COCH2CH2NCH3CH3NHCOCH2CH2N(CH3)2COCH3+HCHO+HN(CH3)2②Ph3PHCHCH3+CHOHHCH3+HCH3H③CH3CH2CH2COCH3+CH3COOC2H5碱CH3CH2CH2COCH2COCH3④CHOH+BrCH2COOC2H5①Zn+C6H6②H2O(C2H5)2OCCHCOOC2H52，完成下列反应式①OCH3+O2NCHOOHH2OH3COHCNO211②OO2Ph3PCHCH3H3CHCCHCH3③O+CH2O(过量)Ca(OH)2H2OOHOH2CHOH2CCH2OHCH2OH④C6H5CHO①(C2H5CH2CO)2O,C3H7COOK②NaOHCHCCOOHC2H5⑤OClCH2COOCH3CH3ONaOCOOCH3H2OOHOCOOHHCHO⑥(EtO)2C=O+C6H5CH2CNC2H5ONaC6H5HCCOOC2H5CN⑦(C6H5)3PCH2CH=CH2ClNaNH2液NH3C6H6回流(C6H5)3PCHCH=CH212OCH2CH2CHOH3CC6H625%OCH2CH2CH=CHCH=CH2H3C⑧CH3CO2CH3O+BrCH2CO2CH3ZnC6H6(C2H5)2OCH3CO2HH2OCH3CO2CH3CHCOOCH33,完成下列合成反应①从甲苯→CCOOEtCOOEtC2H5CH3Br2/hvCH2BrNaCNCH2CNCOOC2H5COOC2H5HCCNOCOOC2H5EtOHHCHCOOEtCOOEtEtONaC2H5BrCCOOEtCOOEtC2H5H+加热CHCOOEtCOOEt②13CH3CH3H2CCH3HCCH3CHOCH3CH3H2CCH3HCCH3CHO①CrO2Cl2CCl4②H2OH3CCHOCH3CH2CHOC2H5ONaH3CCHCCHOCH3Pd-CH2125℃4，填写下列各部产物①α甲基丙醛HCHO/OHA(C5H10O2)HCNH3OB(C6H12O4)+H2OC(C6H10O3)NH2CH2CH2COOCH2PhDH3O+AH3CCCHOCH2OHCH3BH3CCCHCH2OHCH3OHCNCH3CCCHH2CCH3OOOHDH3CCHCCH2OHCH3HNCH2CH2COOCH2PhOHOE(C9H17NO5)+PhCH2OHH3CCHCCH2OHCH3HNCH2CH2COOHOHOE②14COCH3O(C2H5)2NCH2CH2COCH3CH3CH3ONa,CH3OH,C6H6COCH3OCH2CH2COCH3KOHCH3OHH2OH3O+CH3O③OHC①ZnBrCH2COOEt②CH3ONa,CH3OH,C6H6CHCHCOOEtLAHCH2CH2CH2OH①HBr②KCNCH2CH2CH2CNH3OCOOH②AlCl3①SOCl2O第五章氧化反应1，完成下列反应式①CH3NO2CrO3/Ac2OH2SO4CHONO2②15CH3NO2CrO/H2O高温高压COOH③CH3CH3CH3COClAlCl3CH3CH3COCH3①Br2NaOH②H+CH3CH3COOH④HOOHRMnO2CHCl3HOOR⑤OOcAKMnO4,KIO4,H2OBaOH,K2CO335℃OOOAcOH⑥CH3OCH3NO2CH3OCH3NO2CrO2Cl2CS225℃16⑦HOCH2OH(C5H5N)2CrO3CH2Cl2HOCHO⑧0.5MSeO2C2H5OHOH回流⑨H3COOHH3COOHODMSO-DCCH3PO4RTHO⑩ROCROCH3OCCH3OOH2O2NaOH⑾17COOOHClH3CH3CHHHOH(C2H5)2O25℃⑿HCOCH3HOCOCH3C6H5COOOHCHCl32,试以化学表示实现下列变化的各步反应①CHOCHOCOOHC2H5C2H5稀NaOHAg2OCONH2C2H5①SOCl2②NH3RCO3HCONH2C2H5O②HO(CH2)6CH3H3CSO2ClH3CSO2O(CH2)6CH3DMSOOHC(CH2)5CH3③18OH①H2SO4②KMnO4OHOHPb(OAc)4CHOCHO稀NaOHCHO④OH①CrO3H2SO4H2O②SeO2O①KOHBu-tOBu-t②HCl,加热OBu-t第六章还原反应1，完成下列反应①CH3CH=CHCHO0.25MNaBH4CH3CH=CHCH2OH②NO2NH2NH2H2OPd-C/C2H2OHNH2③O0.25MNaBH4or0.25MLiAlH4orMPVOH④OC(CH2)3OCH3OCH3BrOC(CH2)3OCH3OCH3BrZn-HgHCl⑤19B2H6THF25℃2BHH2O2NaOHCH3HHOH⑥H3COOClPb-BaSO4H2Q-SH3COOHCH3CH3⑦2PHCH2CH=CH2+Pd/C2PHCH2CH2CH3+⑧OH2/(Ph3O)3RhClO⑨OOPhH2/Pd-CAcOH,HClO4HOCH2CH2OCH2CH2Ph⑩20NH3COOCCH=CH2NH3COHOHCCH=CH2Al(OCH(CH3)2)3(CH3)2CHOH2,改错①COOEtHOOCLAHC2H6COOEtHOH2CLAHCH2OHHOH2C②CH3COCOOEtZn-HgHClCH3CHOHCOOEt③CH3OCH3H3CHH3CCH3LAHCH3HCH3H3CHH3CCH3HO3，完成下列合成题1，试由环己醇、氯乙酸、乙醇合成H2C(H2C)7CH2C=O21OHCl(CH2)6ClClCH2COOHCH2(COOC2H5)22CH2(COOC2H5)2+Cl(CH2)6ClC2H5ONa(C2H5OOC)2CH(CH2)6CH(COOC2H5)2①②H2ONaOHEtOHH+C2H5OOC(CH2)8COOC2H5NaC6H4(CH3)2refH2C(H2C)7CHOHC=OH2C(H2C)7CH2C=OZn/HClHOAc2，试由OOCH3合成OOOCH30.25MNaBH4OHOCH3H2OH+OHOH+O3，试由COOEtHHCH2CH2COOH制备OO22COOEtHHCH2CH2COOHNaC2H5OHHCH2CH2COONaHCH2OHH+OO第七章重排反应1，完成下列反应式①OHOH稀H2SO4O②CONH2OHHHHOOHHOHHCH2OHNaOCl/H2OCONH2OHHHHOOHHOHHCH2OH③23NC2H5CH2C6H4OCH3CH3C6H5LiEt2ONCH3C2H5CH2C6H9PH2CO+NC2H5CH2C6H5OCH3PCH3④N-ClPhLi/PhHN加热⑤NCH3CH2N(CH3)3NaNH2/NH3NCH3CH2N(CH3)2⑥CH3OHOHCH3H+-H2OCOCH3CH3⑦OCH3CONH2OCH3NaOCl/NaOHOCH3N