Organic chemistry 10Word下载.docx
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Organic chemistry 10Word下载.docx
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-OR(Ar)ester
-NH2、-NHR、-NR2amide
2.NamingCarboxylicAcidsandDerivatives
CarboxylicAcids:
RCO2H
Simpleopen-chaincarboxylicacidsarenamedbyreplacingtheterminal–eofthealkanenamewith-oicacid.The–CO2Hcarbon(thecarboxylgroupcarbon)isalwaysnumberedC1.
Alternativelycompoundsthathavea–CO2Hgroupbondedtoaringarenamedbyusingthesuffix-carboxylicacid.Inthisalternativesystem,thecarboxylicacidcarbonisattachedtoC1ontheringbutisnotitselfnumbered.
3-Bromocyclohexanecarboxylicacid
1-Cyclopentenecarboxylicacid
Commonnames
PopularnameIUPACname(-oicacid)
HCOOHformicacidmethanoicacid
CH3COOHaceticacidethanoicacid
HOOC-COOHoxalicacidethanedioicacid
HOOC(CH2)2COOHsuccinicacid
C17H35COOHstearicacidoctadecanoicacid
C15H31COOHpalmiticacidhexadecanoicacid
Benzoicacid
Nomenclature-oic→oyl
acetylbenzoylpropanoyl
AcidHalides:
RCOX
Acidhalidesarenamedbyidentifyingfirsttheacylgroupandthenthehalide.
Theacylgroupnameisderivedfromtheacidnamebyreplacingthe-icacidendingwith-yl,orthe-carboxylicacidendingwith-carbonyl.Forexample.
AcidAnhydrides:
RCO2COR’
Anhydridesfromsimplecarboxylicacidsandcyclicanhydridesfromdicarboxylicacidsarenamedbyreplacingthewordacidwithanhydride:
AceticanhydrideBenzoicanhydrideSuccinicanhydride
aceticpropanoicanhydride
Amides:
RCONH2
Amideswithanunsubstituted–NH2grouparenamedbyreplacingthe-oicacidor-icacidendingwith-amideorbyreplacingthe-carboxylicacidendingwith–carboxamide.
Ifthenitrogenatomissubstituted,theamideisnamedbyfirstidentifyingthesubstituentgroupandthentheparent.ThesubstituentsareprecededbytheletterNtoidentifythemasbeingdirectlyattachedtonitrogen.
N,N-dimethylacetamide
N,2-dimethylpropanamide
N-phenylacetamide(acetylaniline)
Esters:
RCO2R
Systematicnamesforestersarederivedbyfirstgivingthenameofthealkylgroupattachedtooxygenandthenidentifyingthecarboxylicacid.Insodoing,the-icacidendingisreplacedby-ate:
Nitriles:
R-C≡N
Compoundscontainingthe–C≡Nfunctionalgrouparecallednitriles.Simpleacyclicnitrilesarenamedbyadding-nitrileasasuffixtothealkanename,withthenitrilecarbonnumberedC1.
Morecomplexnitrilesarenamedasderivativesofcarboxylicacidsbyreplacingthe-icacidor-oicacidendingwith-onitrile,orbyreplacingthe-carboxylicacidendingwith-carbonitrile.Inthissystem,thenitrilecarbonatomisattachedtoC1butisnotitselfnumbered:
Acetonitrile(fromaceticacid)Benzonitrile(frombenzoicacid)
2,2-Dimethylcyclohexanecarbonitrile(from2,2-dimethylcyclohexanecarboxylicacid)
3.OccurrenceandPropertiesofCarboxylicAcids
Themostobviouspropertyofcarboxylicacidsisimpliedbytheirname-theiracidity.Carboxylicacidsaremuchstrongeracidsthanalcohols.
Aceticacid:
Ka=1.76×
10-5(pKa=4.75)Ethanol:
Ka=10-16(pKa=16).
carboxylicacidsreactwithbasessuchasNaOHtogivewater-solublemetalcarboxylates,RCO2-Na+.
•
RCOOH>
H2CO3>
ArOH
酸性大小的判断:
1.吸电子能力越高基团的取代烃基上的H则酸性越强
2.吸电子基团越多,酸性越强
3.吸电子基团离羰基越近,则酸性越强
4.斥电子基团越多,越大,则酸性越小
4.NucleophilicAcylSubstitutionReactions
Carboxylicacidsandtheirderivativesalsoreactwithnucleophiles,buttheultimateproductisdifferentfromthatofthealdehyde/ketonereaction.
Incomparingthereactivityofdifferentacylderivatives,themoreelectron-poortheC=Ocarbon,themorereadilythecompoundreactswithnucleophiles.
Aconsequenceofthesereactivitydifferencesisthatit'
susuallypossibletoconvertamorereactiveacidderivativeintoalessreactiveone.Acidchlorides,forexample,canbeconvertedintoestersandamides,butamidesandesterscan'
tbeconvertedintoacidchlorides.
5.ReactionsofCarboxylicAcids.
ConversionofAcidsintoAlcoholsbyReduction(RCO2H→RCH2OH)
carboxylicacidsarereducedbylithiumaluminumhydride(LiAlH4)toyieldprimaryalcohols.
Formationofcarboxylicacidderivatives
acylAcetyl(-ic→-yl)
ConversionofAcidsintoAcidChlorides(RCO2H→RCOCl)
Carboxylicacidsareconvertedintoacidchloridesbytreatmentwiththionylchloride,SOCl2.Theneteffectissubstitutionofthe-OHgroupby-Cl.Forexample:
acylhalideoracidhalide
ConversionofAcidsintoEsters(RCO2H–RCO2R'
)
Perhapsthemostusefulreactionofcarboxylicacidsistheirconversionintoestersbyreactionwithanalcohol-thesubstitutionof-OHby-OR.CalledtheFischeresterificationreaction,thesimplestmethodinvolvesheatingthecarboxylicacidwithanacidcatalystinanalcoholsolvent.
ester(esterification)
Alcohols:
CH3OH>
10>
20>
30
Carboxylicacid:
HCOOH>
CH3COOH>
RCH2COOH>
R2CHCOOH>
R3CCOOH
acidanhydride
Cyclicacidanhydride
amide
6.ChemistryofAcidHalides
ConversionofAcidChloridesintoAcids(RCOCl→RCO2H)
Acidchloridesreactwithwatertoyieldcarboxylicacids(hydrolysisreaction).
ConversionofAcidChloridesIntoEsters(RCOCl→RCO2R'
Acidchloridesreactwithalcoholstoyieldestersinareactionanalogoustotheirreactionwithwatertoyieldacids:
ConversionofAcidChloridesintoAmides(RCOCl→RCONH2)
Acidchloridesreactrapidlywithammoniaandwithaminestogiveamides.
7.ChemistryofAcidAnhydrides
Thebestmethodforpreparingacidanhydridesisbyanucleophilicacylsubstitutionreactionofanacidchloridewithacarboxylicacidanion.
Aceticanhydrideisoftenusedtoprepareacetateestersofcomplexalcoholsandtopreparesubstitutedacetamidesfromamines.
Thechemistryofacidanhydridesissimilartothatofacidchlorides.
8.ChemistryofEsters
ConversionofEstersintoAcids(RCO2R'
→RCO2H)
Estersarehydrolyzedeitherbyaqueousbaseorbyaqueousacidtoyieldacarboxylicacidplusanalcohol:
Hydrolysisinbasicsolutioniscalledsaponification.
soapismadebythebase-inducedesterhydrolysisofanimalfat
ConversionofEstersintoAlcoholsbyReduction(RCO2R'
→RCH2OH)
EstersarereducedbytreatmentwithLiAlH4toyieldprimaryalcohol.
ConversionofEstersintoAlcoholsbyReactionwithGrignardReagents.
Grignardreagentsreactwithesterstoyieldtertiaryalcoholsinwhichtwoofthesubstituentsonthehydroxyl-bearingcarbonareidentical.
9.Chemistryofamides
ConversionofAmidesIntoAcids(RCONH2→RCO2H)
Amidesundergohydrolysistoyieldcarboxylicacidsplusamineonheatingineitheraqueousacidorbase.
ConversionofAmidesintoAminesbyReduction(RCONH2→RCH2NH2)
Likeothercarboxylicacidderivatives,amidesarereducedbyLiAlH4.Theproductofthisreduction,however,isanamineratherthananalcohol:
Thiskindofreactionisspecificforamidesanddoesnotoccurwithothercarboxylicacidderivatives.
Summary
chemicalproperties
nucleophilicsubstitution
HNu:
reaction
H2Ohydrolysis
ROHalcoholysis
NH3(H2NR)ammonolysis
1)hydrolysis
2)alcoholysis
3)Ammonolysis(NH3、H2NR、HNR2)
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- Organic chemistry 10