有機化學(xué)課件chpt1

ChapterPhenolChapterPhenolArylNucleophilicAromaticStructureStructureandNomenclatureDepartmentofXiamenCompoundsthathaveahydroxylgroupdirectlyattachedtoabenzeneringarecalledphenols.4-9 1 821277366534Compoundsthathaveahydroxylgroupdirectlyattachedtoabenzeneringarecalledphenols.4-9 1 821277366534451-萘酚2-萘酚9-菲酚DepartmentofXiamen21.1ANomenclatureof221.1ANomenclatureof23溴苯酚4-22-DepartmentofXiamenDepartmentofXiamen32,4,6-Trinitrophenol(picric2,4,6-32,4,6-Trinitrophenol(picric2,4,6-(苦味酸21,4-苯二(氫醌1,2-苯二1,3-苯二DepartmentofXiamenDepartmentofXiamenRCO23RCO23Methylsaliclate水楊酸甲酯(冬青油(oilof丁子香酚(丁香油DepartmentofXiamenOOO2HHHHZY3(YClOOO2HHHHZY3(YClZ=HAureomycin金霉素(YHZ=OHterramycin土霉素DepartmentofXiamenPhysicalPhysicalPropertiesofDepartmentofXiamenPhenolsarePhenolsarelikealcoholsinbeingabletostrongintermolecularhydrogenPhenolshavehigherboilingpointsthanhydrocarbonsofthesamemolecularweight.AmodestsolubilityinDepartmentofXiamenSynthesisSynthesisofDepartmentofXiamenLaboratoryCu2+,LaboratoryCu2+,(1)NaNO2,H2SO4,0-Cu2+,(2)(80~DepartmentofXiamenHydrolysisofChlorobenzene(Dow 2NaOHHydrolysisofChlorobenzene(Dow 2NaOH(highpressure)+AlkaliFusionofSodiumDepartmentofXiamenFromCumene+CH32250°C,C3OFromCumene+CH32250°C,C3OOC+CumeneDepartmentofXiamenCCHCOOHROOCCCCHCOOHROOCCO+DepartmentofXiamenCOCOCOOOCOCOOCC ++COCOCOOOCOCOOCC ++DepartmentofXiamen21.4CBuchererNaHSO3,NaHSO3,21.4CBuchererNaHSO3,NaHSO3,NH3,PDepartmentofXiamenReactionsReactionsofPhenolsasDepartmentofXiamenStrengthofPhenolsasPhenolisamuchstrongeracidthanpKaStrengthofPhenolsasPhenolisamuchstrongeracidthanpKa=18pKa=9.89GHIGCH3ODepartmentofXiamenDepartmentofXiamenPhenolsfromAlcoholsandCarboxylic++OCH3(CH2)4CH2OPhenolsfromAlcoholsandCarboxylic++OCH3(CH2)4CH2O++DepartmentofXiamenOtherReactionsOtherReactionsoftheO–HDepartmentofXiamenOCOR+++CH(CH)CO322OCOR+++CH(CH)CO322O +DepartmentofXiamenOCArOH+RO+OC+(CH3CO)2O+CO33OCOCArOH+RO+OC+(CH3CO)2O+CO33OCOOR CROC3R+FriesDepartmentofXiamenOCCOO33OC3DepartmentofOCCOO33OC3DepartmentofXiamenOO+COOOOOOOCCOOCOCODepartmentofXiamenOO+COOOOOOOCCOOCOCODepartmentofXiamenPhenolsintheWilliamsonRX+O(X=Cl,Br,I,OSO2OR'orPhenolsintheWilliamsonRX+O(X=Cl,Br,I,OSO2OR'or ++DepartmentofXiamenCleavageCleavageofAlkylArylDepartmentofXiamenconcdRXOR++H2NoDepartmentofconcdRXOR++H2NoDepartmentofXiamenReactionsReactionsoftheBenzeneRingDepartmentofXiamenroom+3+room+3+3DepartmentofXiamen++2+++++2+++DepartmentofXiamen20%+concdconcd20%+concdconcd3DepartmentofXiamenOONHOmorevolatilebecauseofintramolecularhydrogenbondingONOONOlessvolatilebecauseofintrermolecularhydrogenbondingDepartmentofXiamenOONHOmorevolatilebecauseofintramolecularhydrogenbondingONOONOlessvolatilebecauseofintrermolecularhydrogenbondingDepartmentofXiamen SO3H SO3HDepartmentofXiamenReactionwithAcetone—BisphenolOC2+BisphenolOOCHO22CO OExpoxyCDepartmentReactionwithAcetone—BisphenolOC2+BisphenolOOCHO22CO OExpoxyCDepartmentofXiamenOCmOHCOOCOCDepartmentofXiamenOCmOHCOOCOCDepartmentofXiamenReactionwith++or+orReactionwith++or+orDepartmentofXiamenReimer-Tiemann++Reimer-Tiemann++Reimer-TiemannDepartmentofXiamenKolbeCO2CO2+0.5水楊KolbeCO2CO2+0.5水楊OOC CO2HDepartmentofXiamen+0.5CO2 CO2NaCO2+0.5CO2 CO2NaCO2DepartmentofXiamenOOO OOO H2SO4,ODepartmentofXiamenTheTheClaisenDepartmentofXiamenHeatingallylphenyletherto200°CeffectsanintramolecularreactioncalledClaisenrearrangment.OHHeatingallylphenyletherto200°CeffectsanintramolecularreactioncalledClaisenrearrangment.OHo-AllylphenylClaisenDepartmentofXiamen3 CH3OnlyDepartmentofXiamen3 CH3OnlyDepartmentofXia