《货币经纪公司试点管理办法实施细PPT资料.ppt
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《货币经纪公司试点管理办法实施细PPT资料.ppt
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22.722.7ReactionsofAmines:
@#@ReactionsofAmines:
@#@AReviewandaPreviewAReviewandaPreviewPreparationofAminesPreparationofAminesTwoquestionstoanswer:
@#@Twoquestionstoanswer:
@#@1)1)HowistheCNbondtobeformed?
@#@HowistheCNbondtobeformed?
@#@2)2)HowdoweobtainthecorrectoxidationHowdoweobtainthecorrectoxidationstateofnitrogen(andcarbon)?
@#@stateofnitrogen(andcarbon)?
@#@MethodsforCNBondFormationMethodsforCNBondFormationNucleophilicsubstitutionbyazideion(NNucleophilicsubstitutionbyazideion(N33)(Section8.1,8.13)(Section8.1,8.13)Nitrationofarenes(Section12.3)Nitrationofarenes(Section12.3)Nucleophilicringopeningofepoxidesbyammonia(SectionNucleophilicringopeningofepoxidesbyammonia(Section16.12)16.12)NucleophilicadditionofaminestoaldehydesandketonesNucleophilicadditionofaminestoaldehydesandketones(Sections17.10,17.11)(Sections17.10,17.11)Nucleophilicsubstitutionbyammoniaona-haloacidsNucleophilicsubstitutionbyammoniaona-haloacids(Section19.16)(Section19.16)Nucleophilicacylsubstitution(Sections20.3,20.5,and20.11)Nucleophilicacylsubstitution(Sections20.3,20.5,and20.11)Hofmannrearrangement(Section20.17)Hofmannrearrangement(Section20.17)22.822.8PreparationofAminesPreparationofAminesbyAlkylationofAmmoniabyAlkylationofAmmoniaAlkylationofAmmoniaAlkylationofAmmoniaDesiredreactionis:
@#@Desiredreactionis:
@#@2NH2NH33+RXRXRNHRNH22+NHNH44XXAlkylationofAmmoniaAlkylationofAmmoniaDesiredreactionis:
@#@Desiredreactionis:
@#@2NH2NH33+RXRXRNHRNH22+NHNH44XXvia:
@#@via:
@#@HH33NNRRXXHH33NNRR+XX+then:
@#@then:
@#@HH33NN+HHNNHHHHRR+HH33NNHH+NNHHHHRRAlkylationofAmmoniaAlkylationofAmmoniaButthemethoddoesntworkwellinpractice.Butthemethoddoesntworkwellinpractice.Usuallygivesamixtureofprimary,secondary,Usuallygivesamixtureofprimary,secondary,andtertiaryamines,plusthequaternarysalt.andtertiaryamines,plusthequaternarysalt.NNHH33RRXXRRNNHH22RRXXRR22NNHHRRXXRR33NNRRXXRR44NN+XXExampleExampleCHCH33(CH(CH22)66CHCH22BrBrNHNH33CHCH33(CH(CH22)66CHCH22NHNH22Asoctylamineisformed,itcompeteswithAsoctylamineisformed,itcompeteswithammoniafortheremaining1-bromooctane.ammoniafortheremaining1-bromooctane.Reactionofoctylaminewith1-bromooctaneReactionofoctylaminewith1-bromooctanegivesgivesNN,NN-dioctylamine.-dioctylamine.ExampleExampleCHCH33(CH(CH22)66CHCH22BrBrNHNH33CHCH33(CH(CH22)66CHCH22NHNH22(45%)(45%)+CHCH33(CH(CH22)66CHCH22NHNHCHCH22(CH(CH22)66CHCH33(43%)(43%)Asoctylamineisformed,itcompeteswithAsoctylamineisformed,itcompeteswithammoniafortheremaining1-bromooctane.ammoniafortheremaining1-bromooctane.Reactionofoctylaminewith1-bromooctaneReactionofoctylaminewith1-bromooctanegivesgivesNN,NN-dioctylamine.-dioctylamine.22.922.9TheGabrielSynthesisofPrimaryAlkylaminesTheGabrielSynthesisofPrimaryAlkylaminesgivesprimaryamineswithoutformationofgivesprimaryamineswithoutformationofsecondary,etc.aminesasbyproductssecondary,etc.aminesasbyproductsusesanSusesanSNN2reactiononanalkylhalidetoform2reactiononanalkylhalidetoformtheCNbondtheCNbondthenitrogen-containingnucleophilethenitrogen-containingnucleophileisisNN-potassiophthalimide-potassiophthalimideGabrielSynthesisGabrielSynthesisgivesprimaryamineswithoutformationofgivesprimaryamineswithoutformationofsecondary,etc.aminesasbyproductssecondary,etc.aminesasbyproductsusesanSusesanSNN2reactiononanalkylhalidetoform2reactiononanalkylhalidetoformtheCNbondtheCNbondthenitrogen-containingnucleophilethenitrogen-containingnucleophileisisNN-potassiophthalimide-potassiophthalimideGabrielSynthesisGabrielSynthesisOOOONNKK+thepthepKKaofphthalimideis8.3aofphthalimideis8.3NN-potassiophthalimideiseasilypreparedby-potassiophthalimideiseasilypreparedbythereactionofphthalimidewithKOHthereactionofphthalimidewithKOHN-PotassiophthalimideN-PotassiophthalimideOOOONNKK+OOOONNHHKOHKOHN-PotassiophthalimideasanucleophileN-PotassiophthalimideasanucleophileOOOONNRRXX+OOOONNRR+XXSSN22CleavageofAlkylatedPhthalimideCleavageofAlkylatedPhthalimideOOOONNRR+HH22OOHH22NNRR+COCO22HHCOCO22HHacidorbaseacidorbaseimidehydrolysisisimidehydrolysisisnucleophilicacylnucleophilicacylsubstitutionsubstitutionCleavageofAlkylatedPhthalimideCleavageofAlkylatedPhthalimidehydrazinolysisisanalternativemethodofreleasinghydrazinolysisisanalternativemethodofreleasingtheaminefromitsphthalimidederivativetheaminefromitsphthalimidederivativeOOOONNRRHH22NNRR+OOOONHNHNHNHHH22NNHNNH22ExampleExampleOOOONNKK+CC66HH55CHCH22ClClDMFDMFExampleExampleOOOONNKK+CC66HH55CHCH22ClClOOOONNCHCH22CC66HH55DMFDMF(74%)(74%)ExampleExample+CC66HH55CHCH22NNHH2
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- 货币 经纪 公司 试点 管理办法 实施
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