有机合成竞赛习题

有机合成习题有机合成习题 1 合成 MeOOMe MeOMeOOCCOOMe TMMeOOMe MeO MeOOCCCCOOMe OMeO MeO OMe Ph3P CH2 OMe X OMeOH OMe OMe CHO CH3CHO OMe OMe OH OMe OH OMe A OMe OMe OMe OMe OHC BC OMe OMeO I OHOMeOMe CH2Br OMe PPh3 II I II MeOOMe MeO MeOOCCCCOOMe MeOOMe MeOMeOOCCOOMe MeOOMe MeOMeOOCCOOMe A B C Y 答案 A CH3I OH B CO HCl ZnCl2 C CH3CHO OH A CH3I OH B HCHO HBr ZnCl2 C PPh3 LDA Y DDQ 2 写出字母代表的化合物的结构 F ClCl 1 AcCl AlCl3 2 NaOCl A SOCl2 B CH2 COOEt 2 Mg OEt 2 C 1 TsOH 2 EtOH H F ClCl OEt OO HC OEt 3 Ac2O D NH2 E NaH NaOH F ClN COOH O NHNH DMSO TM 答案 ABCD E TM F ClCl COOHF ClCl COClF ClCl O COOEt COOEtF ClCl O COOEt OEt F ClCl O COOEt NH F NN COOH O NH 3 写出字母代表的化合物的结构 O CH3 O 1 HOCH2CH2OH H 2 Ph3P CHCH3 CH3 OO CH3 1 OsO4 2 TsCl A OH B H3O C C13H18O2 Et3N 225 oC CH CH3 O CH3 OD 1 Ph3CLi 2 CH3I E 1 HSCH2CH2SH 2 LiAlH4 3 Hg2 H2O F N2H4 OH 1 Cr VI 2 CH3Li 3 H CH2 CH3 CH3 CH3 答案 CH3 OO TsO OH CH3 ACH3 CH3 O OO B CH3 O CH3 O CD EF O CH3 CH3 O O CH3 CH3 CH3 O OH CH3 CH3 CH3 O 4 写出字母代表的化合物的结构 OO CH3 EtONa O AB C C15H21O4N N H HOOC H H2OH2O CH3 OH O O 答案 CAB OO CH3 CH3 O OO CH3 CH2 N COOH CH3 OH N O COOH 5 写出字母代表的化合物的结构 BrBr NaCN 1 HNO3 2 SOCl2 A B Base C H3O D E C16H12O2 答案 A CNCN B OO ClCl C CN CNO O D COOH COOHO O D O O 6 写出字母代表的化合物的结构 O HCC Na NH3 l OH C CH Hg2 H2O OH CH3 O OMe Cl O AlCl3 A C10H10O2 t BuONa B C18H20O2 答案 AB OMe O O OMe 7 写出字母代表的化合物的结构 CH3 Cl Cl2 PCl5 AB C C22H17N2Cl AlCl3 2C6H6 NH N 答案 CBA CCl3 Cl CClPh2 Cl Ph2CCl N N 8 写出字母代表的化合物的结构 A C12H20O6 CH3 OEt O Br CH2 COOEt 2 EtONa CN EtONa B C15H23NO6 C C17H28O8 EtONa D C15H22O7 1 H2O OH 2 H3O E C7H10O3 1 NaBH4 2 H3O F EtONa G O H H2O I C9H14O3 EtOH H 答案 DEF ABC GHI EtOOCCOOEt COOEtCH3 EtOOC COOEtCH3 COOEt CNEtOOC COOEtCH3 COOEt COOEt COOEt CH3 O COOEt COOEt CH3 O COOH O C CH3 O O CH3 O O CH3 O O O O CH3 OH 9 写出字母代表的化合物的结构 N PhCOCl KCN A H2 Ni 98oC press NH NH Ph O Cl Cl O C6H6 Py B t BuOK 80oC C C19H18N2O2 H3PO4 100oC D CyCOCl Et3N N N O O 答案 AB DC N CNO PhN O Ph NHPh O N N O O Ph N N H O 10 写出字母代表的化合物的结构 NCCH2COOH CH3NHCNHCH3 O A C6H9N3O2 NaOH NaNO2 H2SO4 B C C6H8N4O3 Fe HCl D C6H10N4O2 HCOOH E NaOH F Me2SO4 NaOH N N N N CH3 O CH3 O CH3 Ac2O 答案 ABC E F N NH CNCH3 OO CH3 N N O CH3 O CH3 NHN N O CH3 O CH3 NH N OH N N O CH3 O CH3 NH2 NH2 D N N O CH3 O CH3 NH2 NHH O N N N H N CH3 O CH3 O 11 写出字母代表的化合物的结构 NH NO2 OCH3 O OH AB C C10H8N2O3 H H2O 答案 ABC N H N O O CH3 OO N H N O O CH3 OOH N N O O CH3O H 12 写出字母代表的化合物的结构 ABCCH2 COOEt 2 CO NH2 2 EtONa POCl3 D C4H4N2 NH3 l Na 答案 NHNH O OO NN OH OHOH NN Cl ClCl NN ABDC 13 写出字母代表的化合物的结构 O O CHO HNO3 AB C C14H13O4N FeSO4 NH3 H2O AcCH2COOEt EtONa 答案 ABC O O CHO NO2 O O CHO NH2 O O N COOEt CH3 14 写出字母代表的化合物的结构 AB CD OEt OO NH2 CN O 6H Py E C10H12O2N2 HNO3 H2SO4 F C10H11O4N3 PCl5 105oC G C10H10O3N3Cl H2 Pd NaOAc H C10H17ON3 1 HBr 2 OH I C8H13ON3 NaNO2 H2SO4 TM VB6 答案 ABCD EF GHITM O OEt EtO O NH3 EtO CN O N CN OEt OHN CN OEt OH O2N N CN OEt Cl O2N N OEt NH2 NH2 N OH NH2 NH2 N OH OH OH 15 写出字母代表的化合物的结构 BrBr CH2 COOEt 2 EtONa A C10H17O4Br Br2 B C10H16O4Br2 CH3NH2 C C11H19O4N Ba OH 2 DE HCl F C6H11O2N 答案 AB C D EF COOEt COOEt Br Br COOEt Br COOEt N CH3 COOEt COOEt N CH3 O O Ba O O N CH3 COOH COOH N CH3 COOH 16 写出字母代表的化合物的结构 COOEt NH3 A C5H11O2N COOEt B C10H19O4N Base C C8H13O3N PhCOCl D C15H17O4N H2 Ni E C15H19O4N H3O F C6H9O2N G C7H11O2N CH3I 答案 ABC DE FG COOEt NH2 NH EtOOCCOOEt NH COOEt O N O COOEt O N O COOEt OH NH COOEt N COOEt CH3 17 写出字母代表的化合物的结构 CH2Cl OMe OMe KCN A C10H11O2N H2 Ni H3O B C10H15O2N D C10H11O3Cl C PCl5 E C20H25O5N P2O5 F C20H23O4N Pd 200oC G 答案 ABCD E CH2CN OMe OMe OMe OMe NH2CH2COOH OMe OMe CH2COCl OMe OMe OMe OMe NH OMe OMe O FG OMe N OMe OMe OMe OMe N OMe OMe OMe 18 写出字母代表的化合物的结构及该反应历程 N H CHO PPh3 A C8H9N 答案 N CHO H PPh3 N CHO PPh3 N CH3 Wittig A 19 写出字母代表的化合物的结构 MeO COOMe O H3O A H3O B C15H23O2N NH2 答案 MeO OH MeO NH OCH3 CH3 AB 20 写出字母代表的化合物的结构 O CH2 COOEt 2 EtONa A C11H18O5 HOCH2CH2OH H PhNHNHPh B C21H22O4N2 H3O C C19H18O3N2 答案 ABC O COOEt COOEt OO N N O O Ph Ph N N O O Ph Ph O 21 合成 原料碳数小于 3 O N CH3 NH CH3 O 答案 CH3CH3 O n BuLi CH3 OLi CH2 1 CO NH2 2 2 H3O CH3NH2 ONH2 NaOBr OH CH3NH2 ONHOH DCC ON CH3NH2 Ac2O O N CH3 NH CH3 O 22 写出字母代表的化合物的结构 O COOMe CH3 OMeONa A CH2O B C10H8O4 A OH C C19H12O6 答案 ABC O O OO O O CH2OH O O O O O OH 23 写出字母代表的化合物的结构 答案 O CH3 CH3 1 NaH 2 O Cl A C13H16O2 O CH3 CH2OH CH3 24 写出字母代表的化合物的结构 CH3 CH3 Na NH3 l A PhCO3H B 1 Br2 2 t BuOK C C8H10O 答案 CH3 CH3 CH3 CH3 O O CH3CH3 ABC 25 写出字母代表的化合物的结构 O O CHO CH3NO2 Base A COOEt B H2 Ni C C15H17O3N 答案 O O NO2 O O NO2COOEt O O NH O A BC 26 写出字母代表的化合物的结构 COOMe OMe NaH CH2COOMe 2 A COOMe Base BC H2 Pd C HOAc 1 H3O 2 MeOH H D C15H18O5 答案 ABC D OMe O COOMe COOMe OMe O COOMe COOMe COOMe OMe OH OH COOMe OMe OH OH COOMe 27 完成从到的转化 OHOH OH 答案 OHOH OH CrO3 Py O PhCO3H O O LiAlH4 28 完成从到的转化 EtEt OH CHO Et R Et OHCHO R Et 答案 Et Et OH CHO Et R Et OHCHO R Et OH Et Et O CHO Et R HOCH2CH2OH H Et Et O Et R O O O 1 O3 2 Zn H2O H3O CHOCHO EtEt R EtONa 29 写出字母代表的化合物的结构 NH2 HOOC S N H CH3 CH3 O O Ph3CCl OH A DCC B C34H32O3N2S C C15H18O3N2S H3O 答案 NH HOOC S N H CH3 CH3 O O CPh3 N S NH O CH3 CH3 O O CPh3 N S NH2 O CH3 CH3 O O A BC 30 写出字母代表的化合物的结构 O O COOMe A CH3 2CHO 3Al CH3 2CHOH B Br2 CH3OH CD CH3ONa E C12H14O4 答案 O O COOMe H H OH OH COOMe H H OH OH COOMe H H Br MeO O OH H H Br MeO O O OH H H MeO O ABCDE 31 写出字母代表的化合物的结构 CHO OMe OH Br CH3 2CO K2CO3 AB OHCOOH C C21H22O4 答案 AB C CHO OMe O CHO OH MeO CHO OH MeOO OH 32 写出字母代表的化合物的结构 ClCl OH NH2 A Cl Cl O B C14H9ONCl2 C C14H11O2NCl2 1 NaOH 2 H3O 答案 ABC Cl Cl NH Cl Cl N O Cl Cl NH COOH 33 1 合成 2