IG補課用Chapter-14-organic-chemistry(完整版課件)

OrganicChemistryIntroductiontoorganicchemistry(Chapter14)Hydrocarbons(Chapter15)Halogenoalkanes(Chapter16)Alcohols,estersandcarboxylicacid(Chapter17)Carbonylcompounds(Chapter18)YCICASOrganicChemistry課前預(yù)習(xí)認(rèn)真聽講〔做好筆記，每人一個筆記本！〕認(rèn)真獨立的完成每一次作業(yè)〔勤翻課本和筆記〕做完課后章節(jié)的總練習(xí)及Questions!適當(dāng)?shù)淖鲂┱骖}進行強化！幾點要求：YCICASOrganicChemistryChapter14Introduction

toorganicchemistryI.RepresentingorganicmoleculesII.Functionalgroup(官能團〕III.NamingorganiccompoundIV.BondinginorganicmoleculeV.Isomerism異構(gòu)體VI.Organicreactions-mechanism有機化學(xué)反響機理VII、TypesoforganicreactionsYCICASOrganicChemistryI.Representingorganicmolecules1.Empiricalformula〔經(jīng)驗式〕Definition:theformulathattellsusthesimplestwholenumberratioofthedifferenttypesofatomspresentinonemolecule.e.gethaneempiricalformula:CH3Exercise：1.C3H62.C2H6O23.C4H8O4CH2CH3OCH2O2.Molecularformula〔分子式〕

Definition:theformulathattellsustheactualnumbersofeachtypeofatominamolecule.e.gethanemolecularformula:C2H6Exercise：1.propane2.ethanoicacid3.butanolC3H8C2H4O2C4H10Oa.TypesofformulaeYCICASOrganicChemistry3.Structuralformula(結(jié)構(gòu)式〕Denefition:theformulathattellusabouttheatomsbondedtoeachcarbonatominanorganicmolecule.e.gethene(C2H4)CH2=CH2

propene(C3H6)CH2=CHCH3CH2=HCCH3

ethanol(C2H6O)CH3CH2OH

4.Displayedformula〔展開式〕Definition:adrawingofamoleculethatshowsalltheatomsandbondswithinthemolecule.e.gpropene(C3H6)displayedformulaethanol(C2H6O)Exercise：Question2YCICASOrganicChemistry6.3D(three-dimensional)displayedformulagivesthebestrepresentationoftheshapeofamolecule.e.gmethane5.skeletalformula〔鍵線式〕showsthecarbonskeleton(骨架〕only,hydrogenatomesareomitted〔省略〕,otheratomsthatarenotcarbonorhydrogen,andtheirbonds,areincludedintheskeletalformula.e.gpropene(C3H6)butan-2-olOHwedgedlines=bondstickingout;dottedline=bondstickinginto；Anormallineindicatesabondontheplaneofthepaper.Exercise:

Question3YCICASOrganicChemistrynameoffunctionalgroupstructureoffunctionalgroupnamesofexamplesstructuralformulaoftheexamplealkene(烯烴）C=Cethenearene（芳香烴）

benzenehalogenoalkane（氯代烷烴）-X,whereX=F、Cl、Br、IchloromethaneCH3Clalcohol醇-OHmethanolCH3OHaldehyde醛ethanalCH3CHOketone酮propanoneCH3COCH3Carboxylicacid羧酸ethanoicCH3COOHester酯ethylethanoateCH3CO2CH2CH3amine胺-NH2methylamineCH3NH2nitrile腈ethanenitrileCH3CNII.Functionalgroup(官能團〕YCICASOrganicChemistryIII.NamingorganiccompoundThelongeststraightchainonthemoleculeisindicatedbyoneofthefollowingprefixes:

Numberofcarbonatomsinthechainstem-(Prefix)前綴1Meth-2Eth-3Prop-4But-5Pent-6Hex-7hept-8oct-9non-10dec-YCICASOrganicChemistry1.alkane

(stem+ane)烷烴的命名口訣：選主鏈〔最長、最多支鏈的碳鏈〕，稱某烷。編碳位〔最近、最簡、最小〕，定支鏈。取代基，寫在前，注位置，短支鏈。不同基，取代基首字母在前的先寫，相同基，合并算。2-methylbutane2,2-dimethylpropane3-ethyl-2-methylpentanealkylgroup〔烷基〕CH3-methyl〔甲基〕CH3CH2-ethyl〔乙基〕CH3CH2CH2-propyl(丙基〕給以下烷烴命名：2,4-dimethylpentane4-ethyl-2-methylheptane3,5-dimethylheptaneYCICASOrganicChemistry2.alkene

stem+位次+enebut-2-enebut-1-ene2-methylbut-1-ene注：只有一種位次時，位次省略。YCICASOrganicChemistry3poundscontainaringofcarbonatomscyclohexanecyclopentanecyclopentene4.halogenoalkane2-chloro-2-methylpropane1-chloropropanefluorine

→

fluorochlorine→

chlorobromine→bromoiodine→

iodoYCICASOrganicChemistry5.aliphatic〔脂肪族的，無環(huán)的〕alcoholsandketones(arenamedinasimilarwaytoalkene)CH3CH2CH2OHpropan-1-olpropan-2-olCH3CH2COCH2CH3pentan-3-one6.aliphatic(無環(huán)的〕aldehydeandcarboxylicacid(arenamedinasimilarwaytoalkene)HCHOmethanal2-methylbutanal3,4-dimethylpentanoicacidbutanoicacidYCICASOrganicChemistry7.Amine胺8.nitrile腈CH3NH2methylamineCH3CH2NH2ethylaminedimethylamineethanenitrileCH3CH2CNCH3CNpropanenitrileYCICASOrganicChemistry9.Arene〔芳烴〕10.estermethylbenzenemethylmethanoate

ORCH3CH2CO2CH2CH3CH3OOCHethylpropanoate1,2-dimethylbenzene酯基CH3CH2COOCH2CH3propanenitrilepropanal2,2-dimethylpentanepropylaminepropanoicacidpropylethanoateCH3CH(OH)CH3Propan-2-olCH3CH2COCH2CH3Pentan-3-one幾種物質(zhì)的命名P236Q1YCICASOrganicChemistryIV.Bondinginorganicmolecule

Sigmabonds(σ)andPibonds(π)1.σbondσbondsareformedbythelinearoverlapofatomicorbitals.σ鍵是原子軌道“頭碰頭”重疊形成。σbondsaresymmetricalaboutalinejointingthenuclei(原子核，nucleus的復(fù)數(shù)形式〕oftheatomsformingthebond.σbondscanrotatefreely.YCICASOrganicChemistry2.πbondπbondsareformedbysidewaysoverlapofporbitals.原子軌道“肩并肩”重疊。πbondsarenotsymmetricalaboutalinejointingthenucleioftheatomsformingthebond.πbondrestricts(約束，限制〕rotation.πbondisoftendrawnastwoelectronclouds.answer:BYCICASOrganicChemistry3.Theshapes〔構(gòu)型〕ofsomeorganicmolecules

(ethaneandethene)Ethane

allbondsareσbonds;theshapearoundeachcarbonatomistetrahedral;bondangle:109.5?carboninalkaneissp3hybridization(雜化〕.YCICASOrganicChemistryEthenecontainsσbondandπbond;thebondangleH-C-His117.5?,thebondangleH-C-Cis121?;thecarboninetheneissp2hybridization（雜化）;etheneisplanarshape.π

bonds

σbond117.5?121?YCICASOrganicChemistry

V.Isomerism

(contains

structural

isomerism

and

stereoisomerism(立體異構(gòu)).1.Structuralisomerism〔結(jié)構(gòu)異構(gòu)〕Definition：Compoundshavethesamemolecularformulabutdifferentstructuralformula.Threetypes:a.chainisomerismb.functionalgroupisomerismc.positionisomerism

a.chainisomerism:

C4H10

C5H12b.Functionalgroupisomerisme.g1

carbonylcompoundC3H6O

CH3CH2CHO

CH3COCH3c.

Position

isomerisme.g1.

alcohol

C3H7OHCH3CH2CH2OHCH3CH(OH)CH3Howmanystructuralisomersarethereofchlorobutane,C4H9Cl?answer:4C4H10O(alcohol)所有的structuralisomerism〔結(jié)構(gòu)異構(gòu)體〕Answer:CYCICASOrganicChemistry2.Stereoisomerism〔立體異構(gòu)體〕Denifition:Compoundshavethesamestructuralformulabutwithdifferentarrangementsoftheatomsinspace.Twotypes:cis-transisomerism〔順反異構(gòu)體〕opticalisomerism〔光學(xué)異構(gòu)體〕

i).conditionsforcis-transisomerismrestrictedrotationabouttheC=Cdoublebond.twodifferentgroupsoratomsbondedtoeachcarboninvolvingtheC=Cdoublebond.

Ifanalkylgrouporatomotherthanhydrogenisattachedtoeachcarbonthentheisomerscanbenamedeither

cis(‘onthesameside’)ortrans(‘ontheoppositeside’).cis-but-2-enetrans-but-2-enecis-1,2-dichloroethenetrans-1,2-dichloroethenee.g1e.g2下面哪一個分子不存在順反異構(gòu)體cis-trans

isomers?

Answer:BOpticalisomerism〔Anotherformofstereoisomerism〕opticalisomersofthe

aminoacidalanineChiralcentre:Acarbonatombondedtofourdifferentatomsorgroupsofatoms.e.g:Ifamoleculecontainsacarbonatomthatisbondedtofourdifferentatomsorgroupsofatoms,thenitcanformtwoopticalisomers.YCICASOrganicChemistryopticalisomerisme.g:CHBrCl(OH)CH3CHBr(OH)Answer:1,2,3Answer:DAnswer:DAnswer:DVIorganicreactions-mechanism有機化學(xué)反響機理a.twotypesofbondbreaking:homolyticfission〔均裂〕heterolyticfission〔異裂〕

i.Homolyticfission:Denefition:Whenacovalentbondbreaks,thetwoelectronsinthebondaresharedbetweenthetwoatoms.arefreeradicals（自由基）.andAllfreeradicalshaveanunpairedelectron.ii、HeterolyticfissionHeterolyticfission:Whenacovalentbondbreaks,themoreelectronegativeatomtakesboththeelectronsinthecovalentbond.Electronegativity(電負(fù)性〕:theabilityofanatomtoattractthebondingelectronsinacovalnetbond.ElectronegativityincreasesacrossaperiodfromGroup1toGroup17;(同一個周期，從第一主族到第十七主族，電負(fù)性越來越強；)Electronegativityincreasesupeachgroup;(同一個主族，從上到下，電負(fù)性越來越弱；)curlyarrowshowsthemovementofapairofelectrons.Cation陽離子:anegativelychargedion;Anion陰離子:apositivelychargedions;Alkylioniscalledacarbocation(碳正離子〕.e.g.CH3+、CH3CH2+Duetotheinductiveeffectofalkylgroup,

themorealkylgroupsadjacenttothepositivelychargedcarbonatom,themorestablethecarbocation.Carbocationisanexampleofaspeciescalledanelectrophile.Anelectrophileisanacceptorofapairofelectrons.A