1、+H2OCCHOHH+CC+H2OCCH+CCHOH(A)EYEYYEYEE+E+（A），（），（B）称为）称为AdE2（双分子亲电加成反应）（双分子亲电加成反应） (B)E YCCC CYC CE Y+E(C)EYCCCCYEYECCEYYE+2+R2CCHRHXR2CCHRHXR2CCH2RR2CHCHRXXR2CCH2RXR2CHCHRX有利不利CCHHHCl+ YCCHHHClY或CCHHHClY（I）（II）CHCH2F3CAlBr3(CH3)3NCHCH2F3CCH2CH2Br(CH3)3NCH2CH2I+ HBr+ HI+CCHXHXH+CCHXXCC+HXCCHX快慢HXXHX
2、HCCHX+CCXHCCXHArHCCHRXArHCCHRHArHCCHRHX+ HX+CCHHCH3H3CBrBrBr慢HHCH3H3CBrCC+或（ ）外消旋体CCBr+HHCH3CH3CH3BrHHBrCH3HBrBrHCH3CH3快BrBrCCX2CC X+CCXCC BrSbF6 CCHH3CHPhBrH2CCHCHCH2H+H2C CHCHCH2H（1）（2）（3）+慢CH2CHCHCH2HCHCHCH2HCH2（2）Cl快CH2CHCHCH2HClCH2CHCHCH2HCl（4）（5）+()()+BrCH2CHCHCH2+ BrCH2CHCHCH2BrCH2CHCHCH2Br+C
3、H2CHCHCH2BrBrCH2CHCHCH2BrCH2CHCHCH2BrBr+CH2CCHCH2CH3CH3CCHCH2CH3BrCH3CCHCH2CH3BrHBr1，2 加成1，4 加成HBrPh CHCHCHCH3BrCHCHCH2CHPh+CHCHPhCHCHPhPh CHCHCHCH2BrBrPhPh CHCHCHCH2BrPhBr4%BrBrCHCHCH2CH2CHRRXCRR CCHXHHRRRCHCHR + HX +HXRRRRXH ClCH2CH2CH2CCH3OCCH3ONaOH + NaCl + H2ORCH2CH2OHRCH2CH2X + H2ORCHCH2 + HX
4、+ H2O取代消除HX +RCH2CH2OHRCHCH2 + HX + N(CH3)3RCH2CH2N(CH3)3 + OH取代消除RCH2CH2XHORCHCH2 + X + H2ORCH2CH2OH + X+取代消除CLCH+ B-CLCHBCC+ BH + L-ArCHCH2 + BrOEt + ArCH2CH2BrHOEt +CCHBL CCCCHBL (II)(I)C6H5C6H5CH3HBrHC6H5HBrC6H5CH3HBCH3C6H5HC6H5(1R,2R) C6H5C6H5CH3HBrHHC6H5BrC6H5CH3HBCH3C6H5C6H5H(1R,2S) CCClHO2CH
5、CO2HCCCO2HCO2HCCClHCO2HCO2HCCCO2HCO2H+ HCl碱+ HCl碱；反式比顺式快48倍(III)HHMeHHClCHMe2H(II)HHMeHClHCHMe2H(I)HHHMeHClHCHMe2(V)MeCHMe2(IV)MeCHMe2100%1234123425%氯化萜氯化新萜HXMROCC+ ROH + M + XBrCH3CH3H3CCH3t-BuOK苯二环己基-18-冠-6-醚顺/反 消除比 = 55.0顺/反 消除比 = 0.12CCHNHMeORCCHNR2H3CCCHNR2CH2OHCC+ CH3NR2 ORHSArOOHRHCCRHRH顺式烯烃B
6、反式消除 BrRHRHHCCRHHR反式烯烃B反式消除CHCLCCCHC+- L-, 慢- H+, 快 慢+C(CH3)3CH2CH3CH3C+H+快 (CH3)3C-Br(CH3)3C+ + Br第一步B +CCXHk1k-1CCX+ BH第二步CCXk2CC+ X OAcPhHNO2 OAcPhNO2:_ PhNO2+ CH3O- CH3COO-HCF3CF3CF2CHCHXCH3RRCCHCH3RRCHCHCH2RR+ HX+ HX（查依采夫定则）（霍夫曼定则）Me3CCH2CMe2ClMe3CCH2CCH3CH3Me3CHCCMe2Me3CCH2CCH3CH2(81%)(19%)（查依
7、采夫产物）（霍夫曼产物）CHCHCH3S(CH3)2CH3H3CCCHCH3CH3H3CCHCHCH2CH3H3C查依采夫产物 14%霍夫曼产物 86% 较大酸性较小酸性CH2CHCH3N(CH3)2PhCH2CHCH2PhCHCHCH3 主要CH2CCH2H3C查依采夫产物 81%霍夫曼产物 19%H3CCH2CCH3BrCH3 H3CCHCCH3CH3CH3CH3CH2CH2CH2CHCH3Ft-BuO-CH3CH2CH2CH2CHCH2BrBr不能发生消除反应CCH3H3CCH3Br溶剂解只得19%消除产物t-BuOKt-BuOKn-C18H37Br85%消除作用n-C18H37OTs9
8、9%取代作用B +HCCXCCHBXHCCXBSN2E2HCCXSN1E1- XHCC+ B+ BHCCBHCCBOORH+ORHOCCHXCCHX+HXCHMe2HHOCCH3HHHMeOCHMe2MeCHMe2Me+65%35%AcOPhHHPhDDPhPhHCH3H3CCH3CHCH3OHCH3H3CCH3CHCH3OCSSCH3CH3H3CCH3CHCH2OHSRSCCCOSRHS+RSH + COSNR2HOCCONR2H+CH3CH2CHCH3OCOCH3CH3CH2CHCH2CH3CHCHCH3+HCOOEtHHHOAc(I)MeHHHOCSSMeH(III)(IV)(II)MeCOOEt(V)Me +Me2CHCHMeOAcMe2CHHHHOAcH(VI)Me2CHCHCH2MeMeHMeOAcHMe2CCHMe+
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