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1、CH17:AlcoholsandPhenolsReneeY.BeckerCHM2211ValenciaCommunityCollege1AlcoholsandPhenolsAlcoholscontainanOHgroupconnectedtoasaturatedC(sp3)TheyareimportantsolventsandsynthesisintermediatesEnolsalsocontainanOHgroupconnectedtoanunsaturatedC(sp2)PhenolscontainanOHgroupconnectedtoacarboninabenz
2、enering2AlcoholsandPhenolsMethanol,CH3OH,calledmethylalcohol,isacommonsolvent,afueladditive,producedinlargequantitiesEthanol,CH3CH2OH,calledethylalcohol,isasolvent,fuel,beveragePhenol,C6H5OH(“phenylalcohol”)hasdiverseuses-itgivesitsnametothegeneralclassofcompounds3NamingAlcoholsGeneralcla
3、ssificationsofalcoholsbasedonsubstitutiononCtowhichOHisattached4IUPACRulesforNamingAlcoholsSelectthelongestcarbonchaincontainingthehydroxylgroup,andderivetheparentnamebyreplacingthe-eendingofthecorrespondingalkanewith-olNumberthechainfromtheendnearerthehydroxylgroupNumbersubstituentsaccor
4、dingtopositiononchain,listingthesubstituentsinalphabeticalorder56ManyAlcoholsHaveCommonNamesTheseareacceptedbyIUPAC7Example1:GivetheIUPACnamesforthesecompounds21348Example2:Drawthefollowingstructures2-Ethyl-2-buten-1-ol3-Cyclohexen-1-ol1,4-Pentanediol9NamingPhenolsUse“phene”(theFrenchname
5、forbenzene)astheparenthydrocarbonname,notbenzeneNamesubstituentsonaromaticringbytheirpositionfromOH10PropertiesofAlcoholsandPhenols:HydrogenBondingThestructurearoundOofthealcoholorphenolissimilartothatinwater,sp3hybridizedAlcoholsandphenolshavemuchhigherboilingpointsthansimilaralkanesanda
6、lkylhalides11AlcoholsFormHydrogenBondsApositivelypolarized?OHhydrogenatomfromonemoleculeisattractedtoalonepairofelectronsonanegativelypolarizedoxygenatomofanothermoleculeThisproducesaforcethatholdsthetwomoleculestogetherTheseintermolecularattractionsarepresentinsolutionbutnotinthegasphase
7、,thuselevatingtheboilingpointofthesolution12PropertiesofAlcoholsandPhenols:AcidityandBasicityWeaklybasicandweaklyacidicAlcoholsareweakBr?nstedbasesProtonatedbystrongacidstoyieldoxoniumions,ROH2+13AlcholsandPhenolsareWeakBr?nstedAcidsCantransferaprotontowatertoaverys
