第一章卤化反应1，写出下列反应的主要产物（或试剂）①CH3OC6H4C H CHBr2CCl42~5℃C6H4OH3②OH3C CH3OO CH3CH3BrBrOOCCl4ref 5fOH3C CH3Br③④OBr Me ⑤HOHHI (C H)PIC6H6 ref⑥OO ⑦ICH2COOMe AgFFCH2COOMe⑧COCH3⑨BHI 23CH 3OHCH 3CH 2CHICH 32,写出下列反应可能产物 ①(CH 3)3CCH 2OH3)2CCHCH 3+(CH 3)2CHCH 3CH 3+(CH 3)3CCH2Br②CH 3CCCOOCH 3CH 3NBS,(C 6H 5CO)2O 24HCBrH 2CC3CH 3HCH 3CCCOOCH 3CH 2Br H③CH 3CCH 2CH 2CH 3O23240~45℃CH 3COCH 2 CH 2CH 3CH 2COCH 2CH 2CH 3BrBr④CHCC 2H 5CCH 3CCH 3Cl 2,CH 3COOH 25℃Cl C 2H 5CCH 3COCOCH 3C 2H 5CC H 3CCl OCOCH 3C 2H 5++3，写出下列反应的主要试剂及条件①C(CH 2OH)3C(CH 2Br)4②HOOC(CH 2)4COOH SOCl /RefClCO(CH 2)4COCl③PhCH 2COCH 3SOCl 2/Refor,Cl 2/加热PhCHCOCH 3Cl④O COOH Oor I2/LTA/CCl4/refHgO/I2/加热or AgNO3I2加热第二章烃化反应4，完成下列反应①COOCH3OH OH3COOCH3OCH3OH②OHOCH3OHMe2SO4K2CO3OCH3OCH3OH③H3C H2COCH2CH3OH,H2SO43ONaH3CH2COCH3CH2OH3CH2COHCH2OH④(H2C)5CNHO Me SO(H2C)5CNCH3O⑤NO2ClO2N2NO2NHPhO2N ⑥HOHH3CC6H4SO2OHCH C H SO Cl(EtO2C)2HCHCH2(COOC2H5)2C2H5ONaC2H5OH⑦NHNHCH2⑧O H3C2,完成下列反应过程 ①O CC ON CH(COOC 2H 5)2O CC OC(COOC 2H 5)2Na C 2H 5ONa 25ClCH 2COOC 2H 150~160℃O CC ON C(COOC 2H 5)2CH 2COOC 2H 52CH 3COOHH 2NCHCOOHCH 2COOH②CHO+CH 3NH 2H 2/Raney-NiCH 2NHCH 3OCH 2NCH 3CH 2CH 2OH③C 6H 5CH 2NH 2(C 2H 5O)2PHOC 6H 5CH 2NHP(OC 2H 5)2O2CHCH Br/50%NaOH (n-C 4Hg)4NHSO 4C 6H 5CH 2NP(OC 2H 5)2OCH 2CHCH 2C 6H 5CH 2NHClCH 2CHCH 2④OCH 3(H 3C)3C266NCH 3(H 3C)3CN CH3(H 3C)3CMgBrCCH 3OCH 3(H 3C)3CCH 2C=CH 2CH 3第三章 酰化反应①H 3COOCH 3OCH 3+CH 3COClAlCl 3H 3COOCH 3OCH 3C CH 3O②C C CH 2OHO 2NHOHNHCOCHCl 2H+CH 3(CH 2)16COClN/C 6H 6C C CH 2OOC(CH 2)16CH 3O 2NHOHNHCOCHCl 2H③ClCH2CONHS CCOOHNOCH3+H2NNSNNCH3 OH2C SNNSNNNCH3 OH2C SClCH2CONHS C NOCH3OC④CH3CH3(CH2)5COCl AlCl3ClCH2CH2ClCH3CH3O⑤OCH3 H3COH3CO H3CO2①DMF/POCl3②2OCH3H3COH3COH3COCHO⑥+C6H5N CHOCH3H OPOCl390~95℃CHO⑦CH 3COCH 2COOC 2H 5+HO140℃H 3CCOCH 2COO2，完成下列合成路线 ①OH24或25OC 2H 5DMF POCl 3OC 2H 5CHOCl 2OC 2H 5COClNSOH 2NCH 3CH 3COONaNSONHCH 3CH 3COONaOC 2H 5OC②以苯和丁二酸为起始原料合成四氢萘+OOO3CH 2CH 2COOHOHClCH 2CH 2CHOOHZn Hg HCl第四章 缩合 ①COCH 3+HCHO +CH 3NHCOCH 2CH 2NCH 3COCH 2CH 2NCH 3CH 3NHCOCH 2CH 2N(CH 3)2COCH 3+HCHO +HN(CH 3)2②Ph 3PHCHCH3+CHO3+HCH 3H③CH 3CH 2CH 2COCH 3+CH 3COOC 2H 5碱CH 3CH 2CH 2COCH 2COCH 3④CHO H+BrCH 2COOC 2H ①Zn+C H ②H 2O(C 2H 5)2O CCHCOOC 2H 52，完成下列反应式 ①OCH 3+O 2NCHO OH2H 3COHCNO 2②OO2Ph 3P 3H 3CHC CHCH 3③O+CH 2O (过量Ca(OH)2H 2OOHOH 2CHOH 2CCH 2OH CH 2OH④C 6H 5CHO252237②NaOHC HC C 2H 5⑤OClCH 2COOCH 3CH 3ONaOCOOCH 32OHOCOOHCHO⑥(EtO)2C=O+C 6H 5CH 2CNC 2H 5ONaC 6H 5H C COOC 2H 5CN⑦(C6H 5)3PCH 2CH=CH 2Cl2液NH 3C H回流(C 6H 5)3PCHCH=CH 2O CH2CH2CHOH3C6625%OCH2CH2CH=CHCH=CH2H3C⑧CH3CO2CH3O +BrCH2CO2CH3C6H6 (C2H5)2O32H2OCH3CO2CH3CHCOOCH33,完成下列合成反应①从甲苯→CCOOEtC2H5CH32CH2BrNaCNCH2CNCOOC2H5COOC2H5HCCNOCOOC2H5CHCOOEtCOOEtC2H5Br CCOOEtCOOEtC2H5H+加热②CH3 CH3H2CCH3HCCH3CHOCH3 CH3H2CCH3HCCH3CHO33CCHOCH3Pd-C24，填写下列各部产物①α甲基丙醛A(C5H10O2)H3O6H12O4)+H2OC(C6H10O3)2222DH3O+AH3C C CHOCH2OHCH3BH3C C CHCH2OHCH3OHCNCH3C C CHH2CCH3OOOHDH3C C H CCH2OHCH3HN CH2CH2COOCH2PhOHO9H17NO5)+PhCH2OHH3C CHCCH2OHCH3HN CH2CH2COOHOHOE②32CH2COCH3③第五章氧化反应1，完成下列反应式①CH3NO2CrO3/Ac2OH2SO4CHONO2②CH3NO CrO/H O高温高压COOH③CH3CH33CH3CH3COCH32NaOH②H+CH3CH3COOH④⑤⑥CH3OCH3NO2CH3OCH3NO2 CrO ClCS2 25℃⑦HO CH2OH(C5H5N)2 CrO322HO CHO ⑧0.5MSeO2C2H5OHOH⑨H33⑩⑾H3CH3CHHHOH252⑿HCOCH3HOCOCH3C6H5COOOHCHCl32,试以化学表示实现下列变化的各步反应①CHOC2H525CONH2C2H5①SOCl2②3RCO H CONH2C2H5O②HO(CH2)6CH3H3C SO2ClH3C SO2O(CH2)6CH3DMSOOHC(CH2)5CH3③4CHOCHO 稀NaOHCHO④①KOH -t②HCl,加热OBu -t第六章 还原反应 1，完成下列反应 ①CH 3CH=CHCHO 0.25MNaBH 4CH 3CH=CHCH 2OH ②NO 2NH NH H O Pd-C/C 2H 2OHNH 2③O44or M PVOH④O CO C(CH 2)3OCH 3OCH 3Br⑤B 2H 62BHH 2O 2 NaOHCH 3H OH⑥H 3COOClPb-BaSO 4 H 2Q-SH 3COOHCH 3CH 3⑦2PHCH 2CH=CH 2+Pd/C2PHCH 2CH 2CH 3+⑧O⑨OOPh2AcOH,HClO 4HOCH 2CH 2OCH 2CH 2Ph⑩H 322,改错 ①COOEtHOOCC 2H 6COOEtHOH 2CLAHCH 2OHHOH 2C②CH 3COCOOEt Zn-Hg HClCH 3CHOHCOOEt③CH 3OCH 3H 3C HH 3CCH 3LAHCH 3H CH 3H 3C H H 3CCH 3HO3，完成下列合成题1，试由环己醇、氯乙酸、乙醇合成H 2C(H 2C)7CH 2C=OOHCl(CH 2)6ClClCH 2COOH CH 2(COOC 2H 5)22CH 2(COOC 2H 5)2+Cl(CH 2)6ClC 2H 5ONa(C 2H 5OOC)2CH(CH 2)6CH(COOC 2H 5)2①②H 2O NaOH +C 2H 5OOC(CH 2)8COOC 2H 5Na C 6H 4(CH 3)2refH 2C (H 2C)7CHOHC=O H 2C (H 2C)7CH 2C=O Zn/HCl HOAc2，试由OOCH 3合成OOOCH 30.25MNaBH 4OHO+O3，试由COOEtHHCH 2CH 2COOHCOOEtHHCH 2CH 2COOHC H OHHCH 2CH 2COONaHCH 2OH+第七章 重排反应1，完成下列反应式 ①OHOH②CONH 2OH H H HO OH H OH HCH 2OH2CONH 2OH HH HO OH H OH HCH 2OH③NC2H5CH2C6H4OCH3CH3C6H5LiEt2O N CH3C2H5CH2C6H9PH2CO+NC2H5CH2C6H5OCH3PCH3④N -Cl⑤N CH3CH2N(CH3)323NCH3CH2N(CH3)2⑥CH3OHOH CH3H+2COCH3CH3⑦OCH3CONH2OCH3OCH3NH2OCH3⑧NCEtOOCHNHCEtOOC 180℃⑨OH 3OCH3⑩HO CH2NH2CH3NaNO2/H+OH3C⑾HO33142~147℃8 daysCH 2COOEt⑿CHMe 2Me 2HOCO 2MeMe①HCl-HOAc-Ac 2O ②H 3O CHMe 2CO 2MeMeNH 2二，完成下列合成过程 ①②OCHO+OC 2H 5CH 3OOOOHOCHOOOHCOCH 3CHO③H 2CCH 3EtOCH 3+H 3COOCCH 2OHCH32,4-O 2NC 6H 5OH/Tol 100℃ 8hrOCOOCH 3H CH 3Etclaisen 重排COOCH 3EtOCH 33OHH 2CCH 3OCH 3OCH 3EtOEtEtCOOCH 3CH 3claisen 重排COOCH 3Et OEtCH 3NaBH CH 3OHCOOCH 3EtEtCH 3。