有机化学课件1, INTRODUCTION.ppt

1 FundamentalsofOrganicChemistry DepartmentofPolymerScienceandMaterialsHuaqiaoUniversityXiamen Fujian361021China LinChengE mail cheng Cellphone2 References 胡宏纹 有机化学 高等教育出版社 1990邢其毅 基础有机化学 高等教育出版社 1993JohnMcMurry OrganicChemistry 8thEdition 2010T W GRAHAMSOLOMONS CRAIGB FRYHLE OrganicChemistry 10th Edition 2011裴伟伟 冯骏材 有机化学例题与习题 高等教育出版社 2002 3 CHAPTER1 INTRODUCTION Naturalscience Lifescience MedicineMaterialsscience PolymericmaterialsFinechemicals Chemicalindustry OrganicChemistry 4 Saccharin 1879 3500TimesasSweetasSugar 5 Aspirin Ibuprofen Fullerene 6 7 8 1 1ConceptDevelopmentofOrganicChemistry 1770 OrganicandInorganic T Bergman Sweden 1806 OrganicChemistry J Berzelius 柏则里 Germany 1828 Preparationofureafromammoniumcyanate F Wohler Germany Organicchemistryisthescienceofthecompoundsofcarbon 9 10 1 2StructureandBondingofCarbon 11 12 TheC CsBondinEthane Overlapisalonginternuclearaxistogiveasbond 13 14 15 StructureofAcetylene 16 17 2s 2p sphybrids hybridization 2p 2p N C 18 allene endview Moleculehasatwistinthecenter sp2 sp2 sp 19 1 3BondPolarityandElectronegativity 20 ClassificationofChemicalBonds 21 22 23 24 1 4AcidsandBases 2 TheLewisDefinitionALewisacidisasubstancethatacceptsanelectronpairandaLewisbaseisasubstancethatdonatesanelectronpair 25 Equilibriumfavorsreactionofthestrongeracidandstrongerbasetogivetheweakeracidandweakerbase 26 QuantitativeMeasuresofAcidStrength 1 Theequilibriumconstant Keq forthereactionofanacid HA withwatertoformhydroniumionandtheconjugatebase A isameasurerelatedtothestrengthoftheacid2 StrongeracidshavelargerKeq3 Notethatbrackets indicateconcentration molesperliter M 27 28 OrganicAcids ThosethatloseaprotonfromO H suchasmethanolandaceticacidThosethatloseaprotonfromC H usuallyfromacarbonatomnexttoaC Odoublebond O C C H 29 OrganicBases HaveanatomwithalonepairofelectronsthatcanbondtoH Nitrogen containingcompoundsderivedfromammoniaarethemostcommonorganicbases Oxygen containingcompoundscanreactasbaseswhenwithastrongacidorasacidswithstrongbases 30 31 32 33 34 IllustrationofCurvedArrowsinFollowingLewisAcid BaseReactions ThecombinationofaLewisacidandaLewisbasecanshownwithacurvedarrowfrombasetoacid Acurvedarrowshowsthatapairofelectronsmovesfromtheatomorbondatthetailofthearrowtotheatomorbondattheheadofthearrow 35 1 5 1Bondformation Mostorganicreactionstakeplacebetweennucleophilesandelectrophiles wherethenucleophiliccenterofthenucleophileformsabondtotheelectrophiliccenteroftheelectrophile 1 5 2Classificationofreactions Reactionscanbeclassifiedasacid basereactions functionalgrouptransformationsorascarbon carbonbondformations Reactionscanalsobeclassifiedaccordingtotheprocessormechanismtakingplaceandthesearespecificforparticularfunctionalgroups 1 5ReactionandMechanisms 36 1 5 3Mechanisms Amechanismdescribeshowareactiontakesplacebyshowingwhatishappeningtovalenceelectronsduringtheformationandbreakingofbonds Movementofapairofelectrons Movementofoneelectron 37 DrawingaCurvedArrowfromthesourceofelectronstothedestinationofelectrons R Robinson incorrectn