有机化学（厦门大学） chpt13 含氮芳香化合物

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1、第十三章含氮芳香化合物AromaticNitrogenCompoundsOrganicChemistry13.1芳香硝基化合物XiamenNitroarenesUniversityOrganicChemistry13.1.1结构(Structure)2spOXiamenN127OUniversity147pm121pmOrganicChemistry芳香硝基化合物的共振结构芳香硝基化合物的共振结构ArNO2OONNOO极限式离域式XiamenOOUniversityNNOO共振式OrganicChemistry13.1.2制备(Preparation)¢Wehaveal

2、readyseenmanyexamplesofthepreparationofaromaticnitrocompounds.Byfarthemostimportantroutetosuchcompoundsiselectrophilicaromaticnitrationwithnitricacid.XiamenNO2CH3CH3CH3CH3HNO3UniversityAc2O,20CH3CH3OrganicChemistry13.1.3硝基化合物的性质XiamenPropertiesofNitroCompoundsUniversityOrganicChemistry1

3、3.1.3硝基化合物的性质(PropertiesofNitroCompounds)¢Nitrobenzeneandrelatednitrocompoundsaregenerallyhighboilingliquids.¢Nitrobenzenehaveacharacteristicodorofalmonds.¢NitrobenzeneisreadilyabsorbedthroughtheXiamenskinandispoisonous.Universityb.p.210–211NO2PaleyellowoilOrganicChemistryO2N2,4,6-Trinit

4、rotoluene,CH3NO2TNT,m.p.81O2N¢TNTisanimportantexplosive.ItisrelativelyinsensitivetoshockandisusedXiamenwithadetonator.¢1,3,5-TrinitrobenzeneislesssensitiveUniversitythanTNTtoshockandhasmoreexplosivepower,butismoredifficulttoprepare.OrganicChemistry13.1.4芳香硝基化合物的反应(ReactionsofNitroarenes)

5、NO硝基上的反应2Xiamen芳环上的反应UniversityOrganicChemistryReactivitiesofNitroGroup¢Thenitrogroupisrelativelystabletomanyreagents.¢Itisgenerallyinerttoacidsandmostelectrophilicreagents.Xiamen¢Itisalsostabletomostoxidizingagents.¢ItreactswithRMgXandstronglybasicreagents.University¢Themostimportantrea

6、ctionofthenitrogroupinaromaticcompoundsisreduction.OrganicChemistry还原反应(Reduction)¢Thereductionproductsdependsonthereactionconditionsused.¢Reductionofthenitrogroupactuallyproceedsinaseriesoftow-electronsteps.NO2NONHOHNH2Xiamen2e+2H+2e+2H+2e+2H+H2OH2OUniversityNitrobenzeneNitrosobenzenePh

7、enylhydroxylamineAnilineOrganicChemistry单分子还原单分子还原CH3CH3NO2NH2H2/Nipressure,87~90%CH(CH3)2CH(CH3)2XiamenNO2NH2H2/PtUniversityEtOHC(CH3)3100%C(CH3)3OrganicChemistryCatalytichydrogenationandchemicalreducingagentsinacidicmediagivethecorrespondingaminesinhighyield.CH3CHNO32NH