清华大学有机化学李艳梅老师课件第十章

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1、Chapter10Alcoholsandphenols第十章醇与酚OrganicChemistryA(1)ByProf.LiYan-MeiTsinghuaUniversity醇（Alcohol）酚（Phenol）ContentPartIAlcohols10.1Structure,isomerization,classificationandnomenclature10.2Physicalandspectroscopicproperties10.3Monobasic/Monohydroxylalcohol10.4Polybasicalcohol10.5Preparationof

2、alcohol10.6SourcesandusagesPartIIPhenol/Hydroxybenzene10.7Structureandnomenclature10.8Physicalandspectroscopicproperties10.9Chemicalreactions10.10Preparations10.11SourcesandusagesPartIAlcohols第一部分醇10.1.1Structure10.1.2Isomerization10.1.3Classification10.1.4Nomenclature10.1Structure,isomeriz

3、ation,classificationandnomenclature108.5osp3hybridizationμ≈2DVeryclosetowaterManyalcoholscompletelymisciblewithwater10.1.1Structure结构10.1.2Isomerization异构PositionisomerizationFuctionalgroupisomerizationCarbonchainisomerization位置异构碳架异构官能团异构10.1.3Classification分类C12根据羟基数目：一元醇二元醇三元醇根

4、据所连的碳原子不同：一级醇（伯醇）二级醇（仲醇）三级醇（叔醇）根据所含碳原子数目：低级醇中级醇高级醇10.1.4Nomenclature命名Decidingthelongestchaintowhichthehydroxylgroupisattached1Decidetheserialnumberforallcarbonatoms.2Writedownthename.3123452-pentanolIntermolecularhydrogenbondBoilingpointMeltingpointSimplealcoholscompletelymisciblewithwater

5、与水形成氢键低级醇一般与水任意混溶10.2Physicalandspectroscopicproperties10.2.1Physicalproperties分子间氢键导致熔点、沸点较高Simplealcoholsmayformco-crystalswithinorganicsalts.低级醇与一些无机盐（如：MgCl2、CaCl2、CuSO4等）形成结晶状的分子化合物－结晶醇（醇化物）MgCl2,CuSO4……MgCl2·6CH3OHCaCl2·4C2H5OHCaCl2·4CH3OH用途：除去有机溶剂中少量的醇将醇与其它有机物分开危害：不可用MgCl2、CaCl2、CuSO

6、4等来干燥低级醇10.2.1Spectrometryν(O-H)ν(C-O)3640cm-13630cm-13620cm-11050cm-11100cm-11150cm-1IRν(O-H)3550~3450cm-1ν(O-H)3400~3200cm-1inintermolecularhydrogenbondingsystemsν(-OH)3600~3500cm-1inintramolecularhydrogenbondingsystemsν(-OH)3200~3500cm-1multimoleculeclusterν(-OH)3400~3200cm-1ν(O-H)3710cm

7、-1ν(O-H)3300cm-1ν(O-H)3600~3450cm-1IRofOHbondinwatermoleculeSolid,iceCrystallizedwaterLiquidwaterNMR0.5-5.5~3.715-19活泼氢10.3.1Acidityandbasicity10.3.2Esterifying10.3.3Nucleophilicsubstitution10.3.4Dehydrationandelimination10.3Monobasic/Monohydroxylalcohol