Aromaticcompounds第九章芳香化合物OrganicChemistryA(1)ByProf.LiYan-MeiTsinghuaUniversityContentContentContentContent9.1Structure9.2Classification,NomenclatureandIsomerization9.3SpectrumData&PhysicalProperties9.4ElectrophilicSubstitutionofSubstitutedBenzene9.5OtherChemicalReactionsofSubstitutedBenzene9.6ArylHalides9.7PolycylicAromaticHydrocarbons9.8Aromaticity9.9PreparationofAlkylHalides9.1.1Molecularstructure9.1.2Aromaticlty9.1.3Explanation9.1Structure1.09Å1.39Å120o120oHHHHHH9.1.1Molecularstructure分子结构Aplanerandsymmetricmolecule9.1.2Aromaticity芳香性3H2cat.cat.H23H2cat.CyclohexatrienehypotheticalExperimentalCalculatedExperimentalBenzene1,ValenceBondTheory价键理论观点9.1.3Explanationsp2delocalization-bond2,MolecularOrbitalTheory分子轨道理论观点反键轨道成键轨道反键轨道成键轨道3,ResonanceStructure共振论观点iiiiiiivvviviiviii9.2.1Classification9.2.2Isomerization9.2.3Nomenclature9.2Classification,NomenclatureandIsomerization单环芳烃单环芳烃稠环芳烃多苯代脂肪烃联苯9.2.1Classification分类多环芳烃多环芳烃H12345678910根据芳环的个数根据芳环连接的方式9.2.2Isomerization异构连－均－偏－CH3CH3CH3CH3CH3CH3CH3H3CCH3CH3CH3CH3CH3CH3CH3o-m-p-9.2.3Nomenclature命名方法一：以侧链为母体，以芳环为取代基3-苯基戊烷1-苯（基）乙醇CH3CH2CHCH2CH3OH方法二：以苯环或其衍生物为母体1、一取代衍生物R、X、NO2、NO视为取代基乙（基）苯溴苯亚硝基苯NOBr其它基团与苯环一同视为苯的衍生物-NH2-OH-CHO-COR-SO3H-COOH氨基羟基酰基酰基磺酸基羧基苯胺苯酚苯甲醛苯某酮苯磺酸苯甲酸2、多取代衍生物情况一：只有X、R、NO2、NO这几种取代基关键：以“苯”为母体顺序规则1-硝基-2-氯苯NO2Cl情况二：含有除X、R、NO2、NO之外的其它基团关键：选母体母体官能团确定后，其余基团均为取代基原则：－OR、－NH2、－OH、＝CO、－CHO、－CN、－CONH2、－COX、－COOR、－SO3H、－COOH3-硝基-2-氯苯磺酸SO3HNO2Cl3-氨基-5-溴苯酚NH2BrHO3-羟基苯甲酸COOHOH2-氨基-5-羟基苯甲醛NH2CHOHO9.3.1Spectrumdata9.3.2Physicalproperties9.3SpectrumData&PhysicalProperties9.3.1Spectrumdata7.297.407.277.407.292.601.25012345678PPM144.3127.7128.6125.9128.6127.728.214.5020406080100...
