有机化学第二版王彦广课后答案.pdf

2010-3-162-6(1)CH3(CH2)4CHCH2CHCH2CH3CH3CH3CCHH3CCH3CH3(2)3-3-6-3-5-(112-)(3)HCCCHCH2CH3CH2CHCCH2CH2CH3CH3(4)7-6-3-6-3-5-1-2-7(1)(2)CH2CHCH2CH2CHCH2CH3CHCHCHCHCH3-CHCCH3CH2CHCN-CH2CHCHOCHCCH2CHCH2-78CHCOCH3CH2CHOCH3p-p-CH3COOHCH3CONH2p-p-22)CCHH331-22CCHHCC-C2-8P31(1)(2)DH(E)-3-2-5-(E)-1-33-2-(CH3)2CHCCCH2CH3F(3)CH3CH2(Z)-2-3-4-3-CCCH2CH3CH3CH2CHCH3CH2CCCH2CH2CH3CH2CH(CH3)2H(4)4E7Z-28-7-4-47-CCIFBrClCCMeEti-PrPr-n(5)(6)(E)-1-2-2-1-Z-23-4-3-CH3CHCCHCH2ClCH3CH3CClCCH2CH3CH3(7)(8)CH3Z-24-1-2-Z-3-2-2-HCCCH2CCCH2C(CH3)3CH3(9)CH3CH2Z-577-4-4-1-2-10.HClCH3HClCH3CH3HBrHFCl(1)(2):HHClClH3CCH3HCH3FHClBr:(8)ZZ-3-3-CHCH33Cl8)3-2-2-CHCH33)3334-1-1-ClHCH3HCH3ClHH3CBrHClF:HH3CClHCH3ClHH3CBrHClFCH3HClHCH3C2H5HBrCH3BrCH3H(3)(4):C2H5CH3HHH3CClHHBrBrH3CCH3:HH3CClCH3C2H5HBrHCH3CH3HBr:CH3ClHCH3C2H5HBrHCH3CH3HBr2-11HHH3CHBrH3CHBrFHFH(1)(2):HHHBrCH3H3CHBrFHFH:ClCl3HHHC2H55ClHCHH33HHBrHHHCH3H3CHBrFHFH:HBrHHCH3H3CHBrFHFHCH3CH3HHFH3CH3CHClCH3HCl(3)(4):CH3H3CClHClHCH3CH3HHH3CF:HH3CClCH3ClHCH3HCH3CH3FH:HH3CClHCH3ClCH3H3CHCH3FHBr(1)(2)-35-1010-7-4.3.2-3-(3)(4)2-7-4.58-2.5-5-CHCH33CCHH33CHClHH3CCCHH3HH(5)(6)377-4.1.07-3.52-13Me(1)(2)(3)CH2CH3Bu-tCH3CH3C(CH3)3MeCH3CH2CH3H3CCH(CH3)2MeBu-tMeCH3CH3CH3(4)(5)(6)MeMeBu-tCH3Bu-tMeMeCH3CH3CH3CH3CH3CH3CH3CH(CH3)2CH3CH3CH3(7)(8)(9)H3CCH3CH3CH(CH3)2H3CCH3CH3CH3CH3CH3CH3CH3CH(CH3)2CH(CH3)2(10)(11)(12)CH3CH3H3CCH(CH3)2CH3CH3CH(CH3)233CCHH33CH3CHCHCH(CHCH33)2CHCHP451.(1)-1-4-(2)(2E4Z)-24-Met-Bu(3)33-(4)CCCH3CH2CH=CHCH3(5)(6)CH3CH2CHCH3CH3CH2CCH3CH3CH3HCCH3CH3CHCCH3CH3CH3H3CCH3CH2CHCCH3CH2CH3CH3H3CH3C(7)26-3.4-5-(8)8-4.4.2-2-.CH3H3CH3C2.1CH3CHCH32CH3CH2CHCH33CCH3CH3H3C4CH3CHCH2CH35CH3CH2CH2CH2CH2CH26CCH3CH3CH2H3C7CH2=CHCH281-CH3CH=CH9CH2=CH10HCC112-HCCCH2121-.CH3CCHH4.4.24.2CCH255CCCHH33CHCHCHCHC6.pp41-42HHHHHHHHHHHH123456180pmCH2CH2HHHHHHHH123456HHHHHHHHHHHH123456HHHHHHHHCH2CH2123456C-1C-4180pm240mC-2C-3C-5C-67.13-14-.p27p2813-p-p-p-p-pCCCCHHHHHH13-13-14-13-11.5g50mL10cm20+9315cm250mL150mL10cmDt=lxc1+2.79o2+1.395o3-2(1)(3)(2)CH2H2CCH2H2CClClCOOHHOHOHHCOOH1i23iC23-3RS(1)(2)ClCH2ClCH3CH(CH3)2CH2=CHHBrCH2CH3SR3-4L-(-)-(+)-DLL3-5FishcherRS11234-2234-OHOHHOHOHHOHOHHHOHHORSSRBrBrBrCH3HHC2H5HHHHCH3BrBrC2H5BrHBrBrCH3HHC2H5BrHHBrCH3BrHC2H5Br2R3R4S2S3S4R2R3R4R2R3S4ROHOHOHOHOHHHOHHHHOHOSSRRBrHBrCH3BrHC2H5HBrHHCH3BrBrC2H5HBrBrHCH3HBrC2H5HHBrHCH3HBrC2H5Br2R3S4S2S3S4S2S3R4S2S3R4R8CHCH22=CHCHHHBrBrCHCH22CHCHR+)-23-6FischerRS23CH3HOHCOOHHClBrHCH3HClCH2ClH3CHHOCH3HOH(1)CO2HCH3HOHClHRSRCH2ClCH3HBrClHRRCH3CH3HOHHOHR3-7Fischer1(23)-2-3-2(23)-2-3-CH3CH3BrHClHRSCO2HCO2HHHOHClSRH3CClCH3HO2COHClCO2HBr3meso-23-(4)(12)-2-.CH3CH3BrHBrHRSH3CBrCH3BrHOClClOH3-8OOOOOHMeOOMeOMeRROOOOOHMeOOMeOMeRRHO)HO2CCOHOHCO(122)-2-HOClCl33-9(1)(2)BrClOHOHBrClBrClBrClBrClRSRSRSSROHOHOHOHOHOHOHOHRRSRSRSS3-10CH3CCCH3OOClH3CH2CH2ClCH3(1)(2)CH3CH3OClNO2O2NCO2H(3)(4)1(1)(2)HOCH2CHOHCHOHCH2OHCH3CH(NH2)CHFCH33-5(1)1RCH3CH3HNH2FHRSCH3CH3FHHH2NSRCH3CH3FNH2HHSSCH3CH3HHFH2NRCH3HC4(4)(3)CH3CHBrCHBrCHBrC2H5CH3OCH33-5(2)4CH3OCH3CH3OCH3RSRSCH3OCH3CH3OCH3SRSR(5)(6)ClCH3CH3CHBrCHOClCH3ClCH3RSCHOCH3OHHCHOCH3HHO2.(1)CH3BrHCH3BrHCH3HBrHCH3Br(2)CH3HOHCH3OHHOHHCH3CH3OHH(3)ClClClCl3.(1)ClHClH(2)NHNHHNHNOOO(4)(3)ClH3CClBrClBr3HHHHCHCH3CHCHCH33HH5(5)(6)FClFClCCCCH3OC2H5H3CC2H5O4A(C5H8)AB(C5H10)ABAB5C6H12H2C6H146INHC6H5OHC6H5OHINHC6H5OHC6H5OHNHC6H5OHC6H5OHNHC6H5OHC6H5OHNHC6H5OHC6H5OH74-2-NNHCOHOHIOHOHC6H5C1112345(6)()78CH3CH2CH2CCH+12B2H6H2O2OH-H2OCH3CH2CH2CH2CHO9101112CH3CCH3CH2+HBrH3CBrCH3CH3CH3CHCCH3CH3HClOCH3CHClCOHCH3CH3+CH3CHCCH3CH2CH3+Br2CCl4CH3CHBrBrCH3CH2CH3CH3CCH+HI(1mol)CH3CCH2I(CH3)2CCHCH2CH2CCCH3+HBr(1mol)(CH3)2CCH2CH2CH2CCH3BrCH3CH2CH2CCH+H2OHgSO4H2SO4CH3CH2CH2CCH3OCH3CCCHCHCH3+Br2CBrCH3BrCBrCHBrBrCHCH3BrCH3CH2CCCH3+H2Pd-BaSO4HCH3CH2CH3HCH3CH2CCCH3NaNH3HCH3CH2CH3HCH31)B2H62)H2O2OHCH3OHH2O2OHCH2CH3CH3CH2+B2H6H2OCH3CH3OHOH(HBBrr(+BrBr22)CH+2HH22OO21314151617183.1-6KMnO4OH-HCCCH2CH2CH3KMnO4OHCH3CH2CH2CO2H+HCO2HCO2+H2O7IClHCCCH2CH2CH3ICl(excess)HCCCH2CH2CH3IIClCl5.DielsAlder(1)CH3CCHCH2CH3CH31)O32)Zn-H2OCH3CCH3O+CH3CH2CHO+1)O32)Zn-H2OCH3CH2CCHCH3CH2COOHHCOOH+12O2AgO+1)O32)Zn-H2OOHCCHO2CHO-CHOCH3+HICH3CH2CHCH3ICH3+Br2H3CCH3BrCH2HCCH3C(CH3)2BrO4OHOHCH2CHCHCH33CO2CH3+CO2CH3LiAlH4CH2OHSOCl2CH2Cl(2)CN+CN(3)CHO+CHOPh3P=CH2CH=CH2(4)CHO+CHO(5)+CO2CH3CO2CH3CO2CH3CO2CH3(6)+OOOOOO8.2-2-(1)CH2HOO4CH3H3C+Br2CCl4H3CHCH3HBrBrmeso-(2)CH3CH3+Br2CCl4HCH3CH3HBrBr(3)CH3H3CPhCO3HCH3HH3CHO(4)CH3H3CHOClH3CHCH3HClOH(5)CH3H3CKMnO4OHcoolHCH3CH3HOHOH9.C10H161molKMnO4C10H16O21molH2RaneyNiKMnO4OHOOABCHHOOHHccool5A.10.C4H6CH3CH2CO2HHO2CCH2CH2CO2HHO2CCO2HCH3CH2CCHCHCHH2CCH2ABCKMnO4HCH3CH2CO2HHO2CCH2CH2CO2HHO2CCO2H11.CHCH=CH2CH2H3CCCH3CH2CH2CH3CH3CH2.CH3(1)(2)(3)(4)(5)325412C5H12(1)CCH2ClCH3CH3CH3(2)CH3CH2CHClCH2CH3CH3CHClCH2CH2CH3CH2ClCH2CH2CH2CH3(3)HCCH2CH2ClCH3CH3HCCH2CH2ClCH3CH3ClCCH2CH3CH3CH3HCCH2CH3CH3CH2Cl(4).CCHCl2CH3CH3CH3CCH2ClCH2ClCH3CH33.(CH3)2CHCH2CH3(1)Br2hv(CH3)2CBrCH2CH3(2)CH3CH3Br2hvCH2ClCH3(3)CHCH=CHCl2CH3CH3CClCH=CHCH3CH3CH3(4)NBS(1mol)ROORCH3Br(5)CH3500Br2CH3Brr2hvhv(2(6)CH2CH3HBrROORCH2BrCH3(7)BrCCl3CH2=C(PhCO2)2CH2CH3CH2CH3CH2=CCHClCH3CH2CH3+HCCl3(8)CCl4(PhCO2)2Cl+HCCl3412.32.312162.325(1)(2)(3)(4)Cl22ClClCH3CH3+CH2CH3+HClCH2CH3+Cl2ClCH2CH3+Cl2ClCl2CH2CH32CH3CH2CH2CH3CH2CH3Cl+ClCH2CH3(i)(ii)(iii)(iv)(v)(vi)hvor1i2(ii)(iii)3(i)4i(iv)6.()7CHCl23CH3CHCH3+CCl4+2(i)(ii)(iii)(iv)(v)(vi)hv(CH3)3COOC(CH3)3(CH3)3CO2(CH3)3COCH3(CH3)3COHCH3CCH3CH3+CH3CCH3CH3CCl3CH3CClCH3CH3CCl3CH3CHCH3+CH3+HCCl3CH3CCH3CH3CH3CCH3CH3(CH3)3CC(CH3)32CCl3CCl3CCl3CH3CCH3CH3CCl3+CH3CCH3CH3CCl3(vii)8-HCl2Cl9-H-H10.CHCH3CH2CH2CH2CH3H(1)CH3CH2CH2CHCHCH2(2)-H-HCHH2CHCH2CHCH2.(2)(1)CHCH2CHCH3CH3CHCH3CH3CH3CH2CH2CH3HH25-3-(3-)()-1-2-(4)(3)CH3CHOOHCOOHCH3NO24-3-5-2-(6)(5)CH3CH3ClSO3H15-8-(8)(7)NO2ClNO2NO218-2-4-SO3HCHONO2(9)(10)NH2OHCH33-5-3-4-3.(1)+CH2Cl2AlCl3()(6)6)SSOO33HH8-8-18-(2)+Br2CH2CH3FeCHCH3BrCH2CH3BrCH2CH3Br+CH3CH2CH2OHBF3HF(3)OCH2CH2CH2CClOAlCl3Zn-HgHCl(4)CH2CH2CHCH3OHBF3HF(5)C2H5H3CKMnO4H(6)(CH3)C=CH2HFBF3(CH3)3CC2H5BrAlCl3(CH3)3CC2H5(CH3)3CCO2HK2Cr2O7H2SO4+NO2ClNO2ClNO2Cl2FeHNO3H2SO4(8)CHCH33BFOOBF33HFHFCC22HH5(9)O2V2O5400500oCOOO(10)H2Ni(11)NaNH3(l)CH3CH2OHKMnO4HCO2HCO2H(12)HO2C+OOOAlCl3Zn-HgHClHO2COSOCl2ClOCAlCl3OZn-HgHCl9.(1)CH3CH2CH2ClAlCl3CH2CH2CH3Cl2CH2CHCH3ClCH3CH2CH2ClAlCl3CH(CH3)2(2)CH3CH2ClAlCl3HNO3H2SO4NO2NO2CH2CH3NO2CH2CO2HKMnO4(3)CH3COClAlCl3HNO3H2SO4OCH3OCH3OCH3O2NO2NCOCH3OO2CCCHH2C(4)CH3COClAlCl3Br2FeBrBrCH3OCHNO3H2SO4Zn-HgHClBrCH3CH2BrCH3CH2O2N(5)Cl2FeClCH3Cl2CH2ClAlCl3ClCH2ClCH2ClAlCl32HNO3H2SO4NO2NO2NO2(6)HNO3H2SO4NO2NO2O2N(7)AlCl3ClCH=CH2+CH=CH2(8)CH3COClAlCl3CH3OC+2COCH3CH22ClClNO22HNOHNO33H22SOSO44C11Huckel(1)(2)(3)CH=CH2266(4)(5)(6)8p4(7)(8)(9)26(10)14141231.AlCl3(1)(CH3)2CHClCH(CH3)2AlCl3CH3CClOCH(CH3)2CCH3O1.Br2NaOH2.HClH2OCH(CH3)2COOH2(9)9)63AlCl3CH3CClOCCH3O1.Br2NaOH2.HClH2O(2)HNO3H2SO4CCH3ONO2COHONO2CH3ClAlCl3CH3HNO3H2SO4CH3CH3+NO2NO2KMnO4COOHCOOH+NO2NO2FeCl2(3)CH3H2SO4CH3SO3HClClH2OCH3SO3HCH3ClClFeBr2Zn-HgHClCCH3OCH2CH3CH2CH3Br(4)2.Zn-HgHClAlCl3CH3CH2CH2CClCCH2CH2CH3OOCH2CH2CH2CH3(1)AlCl3CH3CH2CH2CH2Cl(2)CHCH2CH3CH3Cl2FeClH2SO4ClSO3HClSO3HHNO3H2SO4NO2ClNO2H2O(3)3SOSOFeCl22Cl3HHgHClHClKMnO4(4)COOHCOOHFeBr2HNO3H2SO4(5)CH3H2SO4CH3SO3HBrBrH2OCH3SO3HCH3BrBrCH3BrBrNO2HNO3H2SO4H2SO4160oCSO3HSO3HNO2(6)(7)CH3hvBr2CH2Br1.MgEt2O2.CH3CHOCH2CHCH3OHEtOHEtOKCHCHCH3AlCl3CH3CCl2.Br2NaOH3.HClH2OCH3(8)O1.CH3COOH1.PCl3AlCl32.CH3COCH3CH3HNO3H2SO4CH3hvBr2AlCl3H2CNO2(9)CH3NO2CH2BrNO2HNO3H2SO4H2CNO2NO2hvBr21.MgEt2O2.CH3Br(10)Na-HgCH3CH2OHBrBrCH3CH3gEtEt22EtEtOO2.CCHH33CCHOHOCHCHNOCHCH22CCHHCHOHOHCH3C11-1NaOHCH3CH2CH2CH2CH2BrNaOHH2OCH3CH2CH2CH2CH2OH2MgCH3CH2CH2CH2CH2BrMgEt2OCH3CH2CH2CH2CH2MgBr3AgNO3-CH3CH2CH2CH2CH2BrAgNO3ROHCH3CH2CH2CH2CH2ONO2+AgBr4CH3CCNaCH3CH2CH2CH2CH2BrCH3CH2CH2CH2CH2CCH3CCNaCCH35NaCNCH3CH2CH2CH2CH2BrNaCNCH3CH2CH2CH2CH2CN+NaBr6C2H5ONaC2H5OHCH3CH2CH2CH2CH2BrC2H5ONaC2H5OHCH3(CH2)4OC2H57NaI8KOH-CH3CH2CH2CH2CH2BrKOHROHCH3CH2CH2CHCH22(1)CH3CH=CH2NBSNaCNCH2CH=CH2BrCH2CH=CH2CN(5)OHPCl3NaCNClCNCH3CH2CH2CH2CH2BrNaICH3CH2CH2CH2CH2ICH3CH=C(CH3)2(2)HBrR-O-O-RNaICH3CHCH(CH3)2BrCH3CHCH(CH3)2I(4)+Br2(1mol)500oCKOHBr(3)+Cl2KOHClCl5OONNaaCC2HNNBrKKCH2CHCHCH3CHCH22CHCHH5OOHHCHOOHaI(6)CH3CH-CH2CHCH3CH3ClNH3CH3CH-CH2CHCH3CH3NH2(9)CH3CCHNaNH2CH3INH3CH3CCNaCH3CCCH3(10)CCHCCAgCOOHAg(NH3)2+HNO3(11)CH3CH2CCH+CH3CH2MgI1)CH3COCH32)H3O+CH3CH2CCMgI+CH3CH3CH3CH2CCC(CH3)2OH(12)BrMeMgEt2OMgBrMeC6H5BrPd(PPh3)4Et3NMe(13)(CH3CH=CH)2CuLi+CH3CH2CH2BrCH3CH=CHCH2CH2CH331AgNO3C2H5OHa.1-b.2-c.2-2-cba1NaI-a.3-b.2-c.1-d.2-acdb2KOH-a.CH3CH2-C-ClCH3CH3b.CH3CH2-CH-ClCH3c.CH3CH2CH2CH2Clabc3NaCNa.CH3CH2CH2Clb.CH3CH2CH2Brc.CH3CH2CH2Icba(7)CH3CH2CH-CHCH2CH3BrCH3KOHCH3CH2CH=CCH2CH3CH3(8)CH3BrKOH-CH3OMeCHCH33CHCH2CH22HH55OHOH4a.CH3CH=CHCH2CH2Clb.CH2=CHCH2CH2Clc.CH3CH2CH=CHCld.CH3CH2CH=CHCH2Cladbc5SN2a.b.c.BrBrBrbac6SN1BrBrBra.b.c.cba8HBrabcCH3CCH3BrCH2CH3CH3CHCH3CHCH3BrCH3CHCH3CH2CH2Brabc(9)E1CHCH3ClCHCH3O2NCHCH3H3COClClabccab8.(1)CH2=CH-CH2CH(CH3)2CH3C-O-CH2CH2CH3CH3CH2CHCH2CH3CH3CH-CHCH3()CH3CH3(2)(3)OH(4)BrBr1H2CCHCH3HBrCH3CHBrCH3H2CCHCH3Br2CH2BrCH=CH2hvMgEt2O(CH3)2CHMgBrCH2=CHCH2CH(CH3)2CHCHCHCHCl3CHCHCHCHCHCHCH3ClccCHCH-CHCH2CH2H2CCHCH3HOCH2CH2CH3B2H6H2O2OHH2CCHCH3CH3CHOHCH3H2OH2SO4KMnO4CH3COCH31.CH3MgBr2.H2OHCH3CCH3CH3OHHBrCH3CCH3CH3BrAgNO3HOCH2CH2CH3(CH3)3COCH2CH2CH3(3)HCCCH3B2H6H2O2OHCH3CH2CHOCH2=CH2HBrCH3CH2BrMgEt2OCH3CH2MgBrCH3CH2CHCH2CH3OH1.2.H2OH(4)HCCH1.NaNH22.CH3BrHCCH31.NaNH22.CH3BrCH3CCCH3NaNH3(liquid)CH3CH3Br2CCl4CH3CHCHCH3BrBr(11.AC6H10Br2-CCl4BBKOH-CCDiels-AlderCOHC-CHOOHCCH(CH3)CHOABCCH31.O32.ZnH2OOHCCHO+OHCCH(CH3)CHOCCHOMggBrBrCHCH3CHCH22.HHCH31.NNaaNHNH22.CHCHCCHCCH3COOOOH3COO+CH3CCH3ABr2-CCl4CH3BrBrKOH-C2H5OHB12(1)CH3CHCHNaNH2NH3(l)(2)CH3CH2CH2BrCH3CHCNaCH3CHCCH2CH2CH3CHCHNaNH2NH3(l)CHCNaOOHCOCH3(3)OHCCHH2SO4HgSOCHCHNaNH2NH3(l)(4)OCCHH5C2C2H5HCH3CH2BrCHCCH2CH3NaNH2NH3(l)NaCCCH2CH3CH2CH2BrCH3CH2CCCH2CH31.NaNH32.NH3H2OHCH2CH3CH3CH2HC6H5CO3HCHCNaCHCHNaNH2NH3(l)CHCNaCH3CH2CH2CH2BrCHCCH2CH2CH2CH3OOCHCH3CCHHCCOCHCH3CHCCHCH22CHCHHHCHCH3CHCH2Na91(1)CH2CHCH2OHPCCCH2Cl2CH2CHCHOHCO3HCH3OHCH3ONa(2)OOHOCH3CH2OHSOCl2MgO1)2)H3O(3)CH2ClCH2MgClCH2CH2CH2OH(4)CH3CHCH2O+CH3OHHCH3CHCH2OHOCH3CHCH2O+CH3OHCH3ONa(5)CHCH2OHOCH3(6)CH3SHNaOHCH3SCH3CH3SNaCH3I(7)C2H5SC2H5KMnO4C2H5SC2H5OO(8)SCH2CH3CH3CH2ISCH2CH3CH2CH3I2.(CH3)3CCHCH3OHH3PO4(85%)(CH3)3CCHCH2(CH3)2CHCCH2CH3(CH3)2CC(CH3)2+(1)HCHCH33OHOHCH33CCHHOOHOOOHCHCH33OONaNaaOHOHHH55KKMMnO(CH3)3CCHCH3OHH+(CH3)3CCHCH3OH2H2O(CH3)3CCHCH3(a)(CH3)3CCHCH2HH+(CH3)3CCHCH2H+(2)CH2OH+H+H2OCH2OHCH2OH2CH2(a)H+CH2H(b)H+CH2CH3HHH+CH2(C)HCCH3CH3H3CCH2OHHBrCCH3BrH3CCH2CH3(3)CHCH22OHOH+2H+(4)OH-H2O(5)OHOHH2SO4OH+H2OH+OHOHOOH2OHOHHOHO(6)CH3CHCH3OHH+H+H2OH+CH3CHCH3OHCH3CHCH3OH2CH3CHCH3H4(1)(CH3)3COH(CH3)3CCH2CH2OH(CH3)3COH(CH3)3CCH2CH2OHKBr(CH3)3CBrMgEt2O(CH3)3CMgBrO(CH3)3CCH2CH2OMgBrH2O(2)CH3COCH3H3CHCCH3OCH2CH2CH3CH3COCH3H3CHCCH3OCH2CH2CH3Al(OCHMe2)3Me2CHOHCH3CHCH3OHNaCH3CHCH3ONaCH3CH2CH2Br(3)OHOCH3CH3CH(OH)CH3HH33CCHCH33OHOHNaHCCHCH3OOCHCHCHCH3C(4)OCH2CH3OHAl(OCHMe2)3Me2CHOHOCH2CH3OH(1)LDA(2)CH2CH2BrOCH2CH3CHCHOH(5)(6)OOCH3NaOCH3OHOCH3K2Cr2O7H2SO4OOCH3(7)OBr2hvBrCH3CH2OHCH3CH2ONaOPhCO3HOHOO(8)OHH2SO41.O32.ZnH2OOOOOCHCH3332Cr22CrO7(9)OHHOCH3OHH2SO4PhCO3HO(1)CH3MgCl(2)H2OHOHCH3CH2=CH2(10)7.OC2H5(1)NO2NO2O2NOHH2SO4100oCOHHO3SSO3HHNO3OHO2NNO2NO2CH3CH2BrNaOHOCH2CH3O2NNO2NO2(2)Br2FeBr3BrMgEt2OMgBrCl2hvClNaOHEtOHH2OHOHK2Cr2O7H2SO4OMgBrOHH2OHOHOHSOSO33HHHHNONONO3OO2N(7)OHBrBrOHH2SO4OHHO3SOHHO3SBrBrBr2OHBrBrH2SO4H2O9.ABIR1HNMR1AC3H8OIR36003200cm-11HNMR1.1d6H2.2s1H4.0m1HH3CCHH3COH2.2s1.1d1.1d4.0m36003200cm-12BC9H12OIR301016101510825cm-11HNMR7.82HdJ=8.0Hz7.32HdJ=8.0Hz3.82Hq2.23Hs1.13HtOCH2CH3H3C2.2s1.1t3.8q7.3d7.8d11.C10H14OC10H12Br2O1HNMR1.39Hs4.91Hs7.44HmC10H14OC(CH3)3HOBrBrC(CH3)3HOBr2H2O4.9s1.3s7.4mC10H14O3010301016101610Hz3.83.8OOCHCH3.83.833d131LiAlH4OCH3CH2LiAlH4OHCH3CH22H2NiOCH3CH2H2NiOHCH3CH23C6H5NHNH2OCH3CH2C6H5NHNH2CH3CH2NNHC6H54(a)C6H5MgBr(b)H+H2OOCH3CH21.C6H5MgBrOHCH3CH2C6H52.HH2O5NaCNH2SO4OCH3CH2NaCNOHCH3CH2H2SO4CN6HClOCH3CH2CH3CH2OHOCH2CH3CH3CH2HClOCH2CH37Zn(Hg)HClOCH3CH2Zn-HgCH3CH2HClCC66HH55MMNNHCgBrCHCH33CHCH.HH22OOO2.1CH3CH3OCH3OHCH3O1.B2H62.H2O2OHCrO3NHCCNa1.2.H2O2OOHOHTsOHC6H6OO1.NaNH22.MeIOOMeHClH2OMeO3MeOMeOMeOBrCHOOHOHTsOHC6H6MeOMeOMeOBrCHOO4CH3CH2CHO+(CH3)2NHNH2CH3CH2CH=NN(CH3)25CCH2CH2CH3CH2CH2CH2CH3OCH3CH2CH2COClAlCl3Zn-HgHCl6C6H5CCH3OC6H5CCH3OHCN1.NaCN2.H2SO47H3CHHCH3OH3CHHOCCH3OPhCO3HCHCl3OHOHOHOHTsOOHHCC66H66MMeOeOMMeO3)2NNHHNNHH3CHCH22CHCH2CAAlCl8C6H5CCH3OC6H6C6H5C=CH2TsOHOHN+NO9CH3CH2CHO1.CH3(CH2)3MgBrEt2O2.HCh3CH2CCH2CH2CH2CH3OHHCh3CH2CCH2CH2CH2CH3OH2CrO483MeOCO(CH2)4CHO41Cr2O3NCH3CH2CH2CH2CH2BrMgBrEt2OCH3CH2CH2CH2CH2MgBr1.CH2O2.HCH3CH2CH2CH2CH2CH2OHCH3CH2CH2CH2CH2CHO(7)OCNMeOMeO1.NaNH2Et2O2.MeIOMeNaOEtOMeOCH2=CHCOCH3NaOHOOHMeOCNMeNaCNMichaelMichaelCrCrOOCHCH2OH10141OO+KOHMeOHOO2OO+NaOMeMeOHOO3OOO+NaOMeMeOHOOO4OO+NaOMeMeOHOCH3OOCH3O5CN+NaOMeMeOHOOOOCNMMeOCH3NaaOOMMe2.a)CH3CH2CH2CO2HCH3CH2CH2CH2OHLiAlH4b)CH3CH2CH2CO2HCH3CH2CH2CH2OHLiAlH4PDCCH2Cl2CH3CH2CH2CHOc)1-CH3CH2CH2CO2HCH3CH2CH2CH2OHLiAlH4SOCl2CH3CH2CH2CH2Cld)CH3CH2CH2CO2HSOCl2CH3CH2CH2COCle)CH3CH2CH2CO2HSOCl2CH3CH2CH2COClPhMgBrEt2OCH3CH2CH2COPhf)N-N-CH3CH2CH2CO2HSOCl2CH3CH2CH2COClPhNHCH2CH3CH3CH2CH2CONPhCH2CH3g)CH3CH2CH2CO2H(CH3CH2CH2CO)2OAc2Oh)CH3CH2CH2CO2HSOCl2CH3CH2CH2COClCH3CH2CH2CH2OHPyCH3CH2CH2CO2CH2CH2CH2CH3CHCHCH33CHCHCH22COCOClClCH2CHCH22CCOO2CHCHONNPhPhCHCH2CH3.1CO2H1.LiAlD4Et2O2.H2OCD2OH2MeO2CCHOMeO2CHOPh3P=CH2LiAlH43OOEt1.NaOEtEtOH2.H3O+1.KOHH2O2.H3O+OOEtOOOHOO(4)OOOEt1.MeMgI(1mol)Et2O2.H3O+OO()(5)OPOCl3CN85%H3PO4SOCl2NaCNH2SO4OHCNCO2HCOCl(POCl3)(6)OHHO2COOH2PdBaSO4OHOOHH2SO44.12-POOOHOHCNCNOOOCl3CO(CH3)3COHCH3CHCO2HCH3CH3CHCH2OHCH3CH3CH=CH2CH3H2SO41.B2H62.H2O2OHH2CrO4333-(CH3)3COH(CH3)3CBr(CH3)3CMgBr(CH3)3CCO2HHBrMgEt2O1.CO22.H7CH3CH2OHCO2H1.KMnO42.HLiAlH4H2SO4CO2CH293-CO2HCO2EtCO2EtOOEtOHHNaOEtEtOH1.NaOH(aq.)2.H123-6-2-OOOOOCO2EtOCO2EtOCO2EtNaOEt(CH3)2CHBrNaOEtO1.NaOH(aq.)2.HNaOCH3CH3OH5.-4-ABCOCO2EtNaaOOEtEtEEtOHtOHt-BuOHTsClPyt-BuOTsAPhCO2NaDMFt-BuO2CPhNaOHH2Ot-BuOHBTsCl1CH3NHCH2CH2CH(CH3)2(CH)3NCH2CH3Cl(1)(2)N-3-NH2CH3H3CCH2NH2(3)(4)-26-CH3C2H5H2NHN=NCl(5)(6)4-2-NHC2H5N2Cl(7)(8)N-NH2CH3NH2CH3HHCH3CH2CH2CHCH2COOHNH2(9)(10)-23-2(1)NH2CH3CH2NH2CH3CONH2abcbac(2)NH2OCH3NH2ClNH2CH3HNH2abcdadbc(3)FCH2CH2NH2F2CHCH2NH2F3CCH2NH2abcabc(4)NH2NH2CNCNNH2abcabcN-N-CHHH(1010)5NHNH22CH3NHNHCHCHH23-23-CH33CHCH22NHNHbb(5)NHNH2NO2ClNH2abcabc(6)NOONONabccba3PhysostigmineglaucomaPhysostigmineNNMeMeOONHCH3PhysostigmineNNMeMeOONHCH3MeI4(1)CH2Cl1.NaN3DMSO2.LiAlH4Et2OCH2NH2(2)O2NNH21.H2SO4H2ONaNO22.O2NOH(3)COOHNO21.ZnHCl2.NaNO2HCl5CuCNCOOHN2ClCOOHCNCH3OCH=CH2CH2I2Zn-CuEt2O(4)CH3OCH-CH2CH2(5)HCBr3(CH3)3COKBrBrSSOONOeNH211.HH2SS22(6)N2OHCO2HClN=NClOHCO2H(7)MeNMe3MeMeOHMeMe(8)NH2CH2CH2CH2CHONaBH3CNEtOHNH(9)C6H5CCH=CHC6H5OOHNC6H5CCHCHOC6H5NO(10)NH2HNO3H2SO41.HNO22.KINH2NO2NO2I5(2)O2NNHONO2NO2NO2HNO3H2SO450oCHNO3H2SO4100oCNaSHNH2NO2EtOHCH3CH2COCl(4)CH3OOHCH3NHC2H5CH3OClNaN3CH3ON3CH3NH21.2.H2O-CO2-N2CH3CHONaBH3CN22CCHCHCC66HH5NN.HNOHNO2222.KIKINO22NNOO2SOSO44(5)MeCO2HO2NMeNHFe-FeSO4H2SO4MeCO2HH2NMeNHO-H2OLiAlH4(7)OONCH3CH31.HCHO(CH3)2NHHClEtOH2.OH(8)CH3CO2HBrIHNO3CH3NO2CH3NH2ZnEtOHAc2OCH3NHCOCH3Br2CO2HNHCOCH3CO2HNHCOCH3OHCO2HNH2BrKMnO4BrBr1.NaNO2HCl2.KI7.IR3330cm-11H-NMR0.91(tJ=7Hz3H)1.33(s1H)1.52(m10H)2.70(tJ=6Hz2H)3.0(m1H)ppmMSmz()127(M+43)84(100)56(20)1.MeI2.Ag2O