3. 化学化工专业基础知识-有机化合物的命名

1第三讲有机化合物的命名NomenclatureofOrganicChemistrySpecilaizedEnglishforChemistryandEngineering22020/2/2IUPACSystemBeginningwithameetinginGenevain1892,aninternationalsystemfornamingcompoundswasdeveloped.Initspresentform,thesystemrecommendedbytheInternationalUnionofPureandAppliedChemistryissystematic,generallyunambiguous,andinternationallyaccepted.ItiscalledtheIUPACSystem.Geneva[dʒi‘ni:və]日内瓦IUPAC国际纯粹与应用化学联合会32020/2/2Thefieldoforganicchemistryisvast,foritincludesnotonlythecompositionofalllivingorganismsbutalsoofagreatmanyothermaterialsthatweusedaily.Itisphysicallyimpossibleforonetostudythepropertiesofeachofthehundredsofthousandsofknownorganiccompounds.•TheNeedforClassificationofOrganicCompounds42020/2/2Henceorganiccompoundswithsimilarstructuralfeaturesaregroupedintoseriesorclasses.Someoftheclassesoforganiccompoundsarehydrocarbons,alcohols,aldehydes,ketones,ethers,carboxylicacids,esters,carbohydrates,andproteins.Eachoftheseclassesofcompoundsisidentifiedbycertaincharacteristicstructuralfeatures.Classes52020/2/2hydrocarbons,烃类，碳氢化合物alcohols,醇类aldehydes,醛类ketones,酮类ethers,醚类carboxylicacids,羧酸esters,酯类carbohydrates,糖类，碳水化合物62020/2/2Hydrocarbonsarecomposedentirelyofcarbonandhydrogenatomsbondedtoeachotherbycovalentbonds.Severalseriesofhydrocarbonsareknown.Theseincludethealkanes,alkenes,alkynes,andaromatichydrocarbons.1.Hydrocarbonsalkanes,[‘ælkeinz]烷烃alkenes,[‘ælki:nz]烯烃alkynes,[‘ælkainz]炔烃aromatichydrocarbons，芳香烃72020/2/2ClassificationofHydrocarbonsalkadienes,etc.cycloalkadienes,etc.一，Aliphaticcompounds(脂肪烃)92020/2/2RuleA-1.SaturatedUnbranched-chainCompoundsandUnivalentRadicalsRuleA-2.SaturatedBranched-chainCompoundsandUnivalentRadicalsRuleA-3.UnsaturatedCompoundsandUnivalentRadicalsAcyclic102020/2/2RuleA-1.SaturatedUnbranched-chainCompoundsandUnivalentRadicals112020/2/2Alkanes(CnH2n+2)NomenclatureofAlkanesIUPACConventions122020/2/21.1Straight-ChainAlkanes132020/2/2英文名称除了含1到4个碳原子以外，其余均用希腊文和拉丁文的数词加上相应的词尾（-ane）来命名，10个碳原子以上的则在数词前加前缀un、do、tri、tetra、penta等。5~10Alkane=Numberprefix-ane11~19Alkane=Numberprefix-decane21~29Alkane=Numberprefix-cosane31~39Alkane=Numberprefix-triacontane40~90Alkane=Numberprefix-contane142020/2/211~19Alkane=Numberprefix-decane11Undecane12Dodecane13Tridecane14Tetradecane15Pentadecane•16Hexadecane•17Heptadecane•18Octadecane•19NonadecaneExamples1-1152020/2/220Icosane21Henicosane22Docosane23Tricosane24TetracosaneExamples1-2•25Pentacosane•26Hexacosane•27Heptacosane•28Octacosane•29Nonacosane21~29Alkane=Numberprefix-cosane162020/2/2Examples1-330Triacontane31Hentriacontane32Dotriacontane33Tritriacontane34Tetratriacontane31~39Alkane=Numberprefix-triacontane•35pentatriacontane•36Hexatriacontane•37Heptatriacontane•38Octatriacontane•39Nonatriacontane172020/2/2Examples1-420Icosane30Triacontane40Tetracontane50Pentacontane20~90Alkane=Numberprefix-contane•60Hexacontane•70Heptacontane•80Octacontane•90Nonacontane132Dotriacontahectane100Hectane32Dotriacontane182020/2/21.2Univalentradicals•命名烷基时，只需把“基”（-yl）字加在相应的烷烃的字首后。Radical=Alk-ylforexample:CH3-MethylCH3CH2-EthylCH3CH2CH2-PropylCH3(CH2)2CH2-Butyl192020/2/2Examples-25Pentane11Undecane202020/2/2QuestionsA-1-11.Givethenameofthealkanerepresentedbyeachofthefollowinglinestructures:11Undecane4Butane8Octane3Propane212020/2/2QuestionsA-1-22.Givethenameandthelinestructurefortheunbranchedalkanewiththefollowingformulas:C6H14C9H20C2H6C8H18CH4C4H10C10H22•6Hexane•2Ethane•10Decane•9Nonane•8Octane•4Butane•1Methane222020/2/2RuleA-2.SaturatedBranched-chainCompoundsandUnivalentRadicals232020/2/22.1支链烷烃和烷基Univalentradicalsderivedfromsaturatedunbranchedacyclichydrocarbonsbyremovalofhydrogenfromaterminalcarbonatomarenamedbyreplacingtheending-aneofthenameofthehydrocarbonby-yl.命名含支链的烷烃时，可把它们视为直链烷烃，但分別是某些氢（hydrogen）原子被称为烷基的原子取代。命名烷基时，只需把“基”（-yl）字加在相应的烷烃的字首后。242020/2/2Saturatedbranched-chainhydrocarbonbranched-chainhydrocarbon=N-Radical+alkaneforexample:CCCCCCCCCCCCCCCCCCCCC2-Methylbutane4-Ethyl-2,5-dimethylheptane2,2-Dimethylpropane252020/2/2QuestionsA-2-1Namethefivealkanesonthispage.262020/2/2AnswersA-2-1272020/2/2QuestionsA-2-2282020/2/2AnswersA-2-2ThelongestchainisnumberedfromoneendtotheotherbyArabicnumerals,thedirectionbeingsochosenastogivethelowestnumberspossibletothesidechains.Whenseriesoflocants（取代位置）containingthesamenumberoftermsarecomparedtermbyterm,thatseriesislowestwhichcontainsthelowestnumberontheoccasionofthefirstdifference.Thisprincipleisappliedirrespectiveofthenatureofthesubstituents.结构较复杂的烷烃不能用普通命名法命名，只能采用系统命名法。选最长的碳链为主链，从一端向另一端编号，支链作为取代基放在母体名称前，编号时(1)使支链的编号尽可能小,(2)支链的排列按基团的字母顺序。2.3复杂的烷烃PrincipleBranched-ChainAlkanes1.Namethelongestpossiblestraightchaingivetheparentnameforthealkane2.Namethesubstituentgroups–thebranchesCnH2n+1–Alkylgroups(derivedfromalkanes)3-Ethyl-2-methylhexane3.Numberthepositionsofthesubstituentgroupswiththesmallestpossiblenumbers22-methyl2-methylbutane4.Ifmorethanonesubstituentgroupofthesamekindexist,thenumbersaredenotedbyprefixes.2di3tri4tetra5penta6hexatetramethyltetramethylmethanepropane22,2-dimethylpropane5.