廈大-有機課件chpt

Organic廈門大學(xué)化學(xué)化工: OrganicXiamenOrganicXiamen邢其毅、徐瑞秋、周政 OrganicXiamen主OrganicXiamenT.W.GrahamSolomons;CraigB.Fryhle,“OrganicChemistry”,7thed.JohnWiley& ,OrganicXiamen主OrganicXiamen 上下冊，高等教育，1990，北AndrewStreitwieserJr.,ClaytonH.Hesthcock;“IntroductionToOrganicChemistry”;MacmillanPublishingCo.,Inc.,1976;4thed.,1992.J.March,“AdvancedOrganicChemistry”,4thed.,JohnWiley&Sons ,1998.Organic Xiamen第一章緒論OrganicOrganicXiamenTheDevelopmentOfXiamenOrganicOrganicXiamenOrganiccompoundsXiamenOrganicWhatisorganicchemistryOrganicshouldyoustudyitXiamenTheanswersareXiamenaroundyouOrganicOrganicchemistryistheOrganicThecompoundsofcarbonarecentraltolifeonthisplanet.Everylivingorganismismadeoforganiccompounds.XiamenConsiderwhattheworldwouldbelikeifallthecarbonandcarboncompoundswereremovedsuddenly.TheresultwouldbesomewhatlikethebarrensurfaceXiamenLifeisorganicOrganicWeliveinanAgeofOrganicOrganicClothing:wool,cotton,nylon,polyesterRubberandXiamenFarmXiamenOrganicXiamenOrganicchemistryplayanOrganicXiamenImportantindustrialproductsandconsequenthazardousOrganicchlorineOrganicchlorineorganicphosphateOrganicsolventsandresidues,metalslikeZnandHg,forHeavymetals,pigments,organicotherpetroleumOils,phenols,andotherorganiccompounds,lead,salts,acids,OrganicOrganicNaturalinsectattractants—insteadLessreactivecompoundsXiamenrefrigerantsandaerosolpropellant—insteadFreon(thatdestroytheXiamenCarswithmoreefficientcombustionengines—reducethemassiveamountofautomobilepollutantsandgreenhouseOrganicOrganic“3R”andGreen XiamenChemistrylaboratoriesconductexperiments—smallerandXiamenEnvironments-friendlyOrganicOrganicXiamenClearly,organicchemistryisassociatedwithnearlyeveryaspectofourexistence.WewouldbewiseXiamenOrganicOrganicOrganicOrganiccompoundsarethecompoundsofcarbon.有機化合物就是碳的化合物。Xiamen格XiamenOrganicOrganicOrganicXiamenOrganicchemistry:astudyofXiamenOrganicOrganicThecharacteristicsoforganic分子組成容易Xiamen低，一般在Xiamen難溶于反應(yīng)速率比較慢，副反應(yīng)1.1.2Organic Xiamen1.1.2OrganicOrganic十九世紀(jì)初產(chǎn)生，至今約2001777年，瑞典化學(xué)家Bergman機”(organiccompounds)兩大類。Xiamen化學(xué)”Xiamen11Organic純的有機化OrganicXiamen1786)，他一生發(fā)XiamenOrganicXiamenOrganicXiamen從酒石中提取酒石酸OrganicXiamenOrganicXiamenCHOHOrganicXiamenOrganicXiamenOOOOOrganicXiamenOrganicXiamen從蘋果中提取蘋果酸CHCOrganicOrganic Xiamen Xiamen

蟻 醋

OrganicXiamenOrganicXiamen琥珀

C6H5C OrganicOrganic1773年，由尿中發(fā)現(xiàn) 1818年，由植物葉中分離出葉綠素Xiamen XiamenOrganicOrganic XiamenXiamen

年提取分離年經(jīng)歷了 Organic1818年，由植物葉中分離出葉Organic

XiamenXiamen

Chlorophyll葉綠N堿OONNOONN堿OONNOONOrganicHOHN辛可HOHN辛可寧NHOrganic XiamenHOrganicXiamenOrganicXiamen21781年拉瓦錫Lavoisier將他的燃燒提出氮的分析法 定氮法 Liebig進一步改進了分析方法，OrganicXiamenOrganicXiamen廠或里制造。NH4ClNH4ClOO+OOrganicXiamen4Wohler由酸銨加熱合成了尿素1845Kolbe合成了1861年布特 合成了Organic XiamenOrganicXiamenOrganicXiamen1得到了1000多萬種有機化逐步建立和完善了有機化學(xué)OrganicOrganicXiamen1865，Kekule（德）碳原子四價1874，Van’tWoff（荷）及Lebel（法）的1917，Lewis（美）電子對理1931，Huckel（德）芳香結(jié)構(gòu)1933，Ingold（英）化學(xué)動力——飽和碳原子的親OrganicOrganicXiamen1962，福井謙一，“前線軌道理論1965，Woodward—Hoffmann分子軌道1967，Corey逆合成分析1972，Olah碳正離子的系統(tǒng)1978，Lehn超分子化學(xué)（主客體化學(xué)OrganicXiamenOrganicXiamen2化農(nóng)用化功能性有機化有機結(jié)構(gòu)生命有機OrganicXiamenOrganicXiamen31.2Organic Xiamen1.2.1Organic XiamenOrganicOrganic1.XiamenXiamenOrganicOrganicXiamenXiamen

OrganicXiamenOrganicXiamen烷無醛或 羰烯 烯羧羧炔 炔腈 基芳芳磺磺鹵代鹵硝基化合硝醇或羥胺氨醚 醚亞有機化合物的同分異構(gòu)OrganicOrganicXiamenXiamen

立體

OrganicOrganicXiamenXiamenOrganicXiamen有機結(jié)構(gòu)式的表OrganicXiamenHHCHHCHHCHHCHCHCHHCHHOrganicXiamen結(jié)構(gòu)簡式(CondensedOrganicXiamenCH (3)Organic Xiamen(3)Organic虛線－楔線式(Wedge-dashedOrganicHHHHHCHXiamenWedge-dashedwedge-lineXiamenOrganicOrganic XiamenOrganicOrganic按化學(xué)鍵的變化自由基型離子型反 協(xié)同反Xiamen按反應(yīng)形Xiamen Organic反應(yīng)機OrganicReactionXiamen XiamenOrganicOrganicXiamenXiamenOrganicOrganicXiamen的條XiamenOrganic動力學(xué)控制反應(yīng)與熱力學(xué)控制OrganicXiamenXiamenOrganic1.2.3Organic1.質(zhì)子溶劑(protic2.偶極溶劑(非質(zhì)子性偶極溶劑)(polaraproticsolvents)SOXiamen3.非極性溶劑(nonpolarsolvents)OrganicOrganic1.2.4XiamenBr?nsted酸堿Xiamen.5Organic XiamenOrganic誘導(dǎo)效應(yīng)InductiveOrganic

C

誘導(dǎo)效應(yīng)的特Xiamen由電負性不同Xiamen不存在 替現(xiàn)OrganicXiamenOrganicXiamen HCCCHHCCCHHOrganicHCHCCHHXiamen–p共 –Xiamen1.2.6Organic Xiamen1.2.6Organic烴基自由基(AlkylOrganic帶單電子的原子或原ABABA+BXiamenXiamenOOOOO55--85O2 OrganicXiamen OrganicXiamen

40－70

2 ＋OrganicOrganic2Xiamen3.單電子轉(zhuǎn)移的氧化還原反應(yīng)XiamenO++OH-+RC-ORCOrganicOrganicXiamen剛性角錐Xiamen迅速翻轉(zhuǎn)的角OrganicOrganicH+H＝439.3XiamenXiamenOrganicXiamenOrganicXiamen CHCH2CH2>>(CH)3>OrganicOrganic伯碳原子(一級碳原子，primary1°：仲碳原子(二級碳原子，secondary2Xiamen叔碳原子(三級碳原子，tertiary3°：Xiamen季碳原子(四級碳原子，quaternary4°：OrganicXiamenOrganicXiamen含有一個帶6個電子碳原子的原子HHHHHHH3CHOrganicOrganicXiamen離子所需的能量△Xiamen

H＝

H＝

形成甲基碳正離子所需的能△H△H鍵離OrganicXiamenH=439.3+958.1=1397.4OrganicXiamen

mol-OrganicOrganic(CH3)3C>(CH3)2CH Xiame