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有机化学A1主讲教师：李艳梅教授清华大学化学系E-mail:liym@tsinghua.edu.cnURL:第一章绪论OrganicChemistryA(1)ByProf.LiYan-MeiTsinghuaUniversityContentPartIOrganiccompoundsandorganicchemistry------History第一部分有机化合物与有机化学－－历史简介PartIIFundamentalKnowledge第二部分基础知识●Structure,reaction&Classification●Formulas●Nomenclature●NMR,IR,UV&MS1.Organiccompoundsandorganicchemistry第一部分有机化合物和有机化学1.1Introductionandabriefhistory有机化学历史简介1.2Characteroforganiccompound有机化合物的特性1.3Researchfieldsinorganicchemistry有机化学研究领域1.4Themethodstostudyorganicchemistryandhowtolearnorganicchemistry有机化学研究方法及如何学习有机化学课程1.1Introductionandabriefhistory有机化学历史简介有机化学？有机化合物？R1CCNHR2NHOO**nStarch（淀粉）CmHnmvaluearound8Gasoline（汽油）OOCH3OOHCOOH3CCOCH3OHOOHOOCH3OOHSalicylicacidAcetylsalicylicacid乙酰水杨酸（阿斯匹林）FormalinaqueoussolutionofformaldehydeHOHOrganicChemistryintheHistoryTomakehumanbodyintoamummy,formalinwasoftenemployedinancientEgypt.甲醛古埃及人利用有机化合物处理尸体WinewasinventedbeforeXiadynasty.ByZhoudynasty,winehasbecomeveryimportantinsacrificeevents.制酒CH3CH2OH«周礼»VinegarproductionhasalreadybecomeanexpecttechnologybyZhoudynasty.制醋COHOH3CDyeinghasbecomeamimportantindustrybeforeZhoudynasty.染色茜草ThedemiseofvitalismInancientages,mixturesoforganiccompoundswereabstractedfromnaturalproducts.Chinesetraditionaldrug,dye,andperfumeareofthiskind.Bythe18thcentury,somepureorganiccompoundswereobtained.Turtricacidwasobtainedfromgrapejuice,citricacidwasabstractedfromlemonjuice,andureawaspurifiedfromurine.1828,preparationofureafrominorganiccompoundsindicatesthedemiseof“vitalism”.In1806,famouschemist,BerzeliusJ.firstusedtheword“organicchemistry”,andstates,organiccompoundscouldnotbeproducedwithout“vitalforce（生命力）”Thefactthatorganiccompoundscouldbeobtainedfrominorganiccompoundswithoutthehelpoforganismwasnotacceptedforalongtime.In1845aceticacidandin1854esterwereseparatelysynthesizedfrominorganiccompounds,indicatingthefinaldemiseofvitalism.兴趣阅读：Seeappendixfile0001:LetterbetweenWöhlerandhisadviser,Berzelius.Seeappendixfile0002:Wöhler’spaperonsynthesisofureaSeeappendixfile0003:Problemsandanswersontheureasyntheticpaper(fromYaleUniversity)(NH4)+NCO-H2NONH2Ammoniumcyanate氰酸铵Abriefhistory190020001800SynthesisofureaFriedrichWöhlerImportanteventsonorganicchemistry1828Synthesisofurea,indicatingdemiseofvitalismMilestoneoforganicchemistryByWöhler1865BringingforwardthatcarbonisquadrivalentMilestoneofstructuraltheoryByA.Kekulé1874SaturatedcarbonatomssharetetrahedraltopologyInitiationofstereochemistryByJ.H.Van’tHoffInitiationofstereochemistryByJ.A.LeBel1917LewisacidandLewisbasetheoryMilestoneofstructuraltheoryByLewis1931HuckelrulesTheFrontier-orbitaltheoryTheprincipleofconservationoforbitalsymmeteryMeansof“Organicchemistry”“有机化学”的含义Firstciting基于“生命力”学说Basedon“vitalism”,Berzeliusfirstcitedthisword,anddeemedorganiccompoundscouldnotbeproducedwithoutthespecialpower“vitaforce”.1806Definition元素分析结果A.L.LavoisierandVonLiebigJ.F.inventedtheelementalanalysisprotocal.Theyfoundallorganiccompoundscontaincarbon,mostcontainhydrogen,manycontainoxygenandnitrogen.KeküléandGmelindefinedorganicchemistryas“chemistryofcarbonaceouscompounds”将“有机化合物”定义为“含碳的化合物”，则“有机化学”即为“研究含碳化合物的化学”Ofcourse,manycarbonaceouscompoundsarenotorganiccompounds1865Schorlemmer’sdefinition肖莱马的定义Basedonchemicalstructuraltheory,Schorlemmerdefinedorganiccompoundas“hydrocarbonanditsderivatives”,andorganicchemistryas“chemistryofhydrocarbonanditsderivatives”.“碳氢化合物及其衍生物”HintNBNBNBHHHHHH分类的关键：“性质”！而不是“组成”1.Organiccompoundsandorganicchemistry第一部分有机化合物和有机化学1.1Introductionandabriefhistory有机化学历史简介1.2Characteroforganiccompound有机化合物的特性1.3Researchfieldsinorganicchemistry有机化学研究领域1.4Themethodstostudyorganicchemistryandhowtolearnorganicchemistry有机化学研究方法及如何学习有机化学课程1.2Characteroforganiccompound有机化合物的特性结构上CNCSCOCFCClCBrCICP1、碳通常以共价键与其它原子相连CCCCCC2、自身成键能力强3、同分异构现象普遍存在PhysicalPropertiesLowmeltingpoint熔点低Lowboilingpoint沸点低Highvolatility挥发性大Ofteninsoluble多数难溶于水Densityoftenlowerthanwater比重一般比水小ChemicalProperties稳定性不如无机物Lessstable易燃Inflammation反应速度慢Lowreactionrate副反应多Frequentsidereaction化学性质物理性质1.Organiccompoundsandorganicchemistry第一部分有机化合物和有机化学1.1Introductionandabriefhistory有机化学历史简介1.2Characteroforganiccompound有机化合物的特性1.3Researchfieldsinorganicchemistry有机化学研究领域1.4Themethodstostudyorganicchemistryandhowtolearnorganicchemistry有机化学研究方法及如何学习有机化学课程1.3Researchfieldsinorganicchemistry有机化学研究领域•NatureProductChemistry天然产物化学Separated,orextractedchemicalsfromnatureproducts.Eg.Hormones,Auxin,PheromoneHO•StructureDetermination结构测定SpectroscopicNMRIRUltraViolateMassspectrometryNonspectroscopicElementaryanalysis•OrganicSynthesis有机合成nHOSimplecompounds•ReactionMechanism反应机理YXYXXYTransitionStateE•Crossscience与其它学科渗透eg.withlifescienceLifeprocedureisconsistedofchemicalreactionsofbiologicalmolecules,thetransformationofmatterandenergy.Chemicalbiologyaimstoexplorethelifeprocedureonthemolecularlevel.ChemicaltheoriesandmethodsLifesciencewithenvironmentengineeringToreducepollutionToextractusefulcompoundsfrominjurants绿色化学1.Organiccompoundsandorganicchemistry第一部分有机化合物和有机化学1.1Introductionandabriefhisto