Chapter 13 Carboxylic acids.ppt

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1、Chapter13Carboxylicacids13.1Nomenclature13.2AcidityofcarboxylicacidsFactorsaffectingtheacidityofcarboxylicacidsDicarboxylicacids13.3Preparationofcarboxylicacids13.3.1PreparationofcarboxylicacidsbycarbonationofGrignardreagents13.3.2Preparationofcarboxylicacidsbythepreparationandhydrolysisofnit

2、riles13.4ReactionsofCarboxylicacids13.4.1Esterification13.4.2α-Halogenationofcarboxylicacids:Hell-Volhard-Zelinskyreaction13.4.3Decarboxylationofmalonicacidandrelatedcompounds13.5SpectroscopicanalysisofcarboxylicacidsCarboxylicacid:Carboxylgroup（羧基）Acylgroup（酰基）Allofcarboxylicacidderivativesc

3、ontaintheacylgroup.13.1Nomenclature1.eoicacid4-Hexenoicacid（4-己烯酸）2-Hydroxy-2-phenylethanoicacidMandelicacid（扁桃酸）4-Methylhexanoicacid（4-甲基己酸）2.Forthecompoundswithpolyfunctionalgroupcarboxylicacidsoutrankallthecommongroup.Ch.P281P3083-Bromocyclohexane-carboxylicacid(3-溴环己烷甲酸)HY>RCOOH>H2CO3>C6H

4、5OH>H2O>RCH2OH>pka:4~56.381015.7416~19~25~34~5013.2Acidityofcarboxylicacidssp2hybridization,p-πconjugation3-Ethyl-6-methyloctanedioicacid(3-甲基-6-乙基辛二酸)1-Cyclopentene-carboxylicacid(1-环戊烯甲酸)12345StrongerbaseWeakerbaseWeakeracidStrongeracidSodiumbicarbonateRCOOH:Waterinsoluble;RCOO-M+(Carboxyli

5、csalt):WatersolubleCarboxylicacidscanbeseparatedfromalcoholsandphenol.Factorsaffectingtheacidityofcarboxylicacids:InductiveeffectsofthesubstituentspKa0.71.482.854.75Withmoreelectron-withdrawinggroups,acidityofthecarboxylicacidisstronger.Inductiveeffectsfalloffrapidlyasnumberofσbondincreases.P

6、313,10.3pKa:2.854.054.502-Chlorobutanoic3-Chlorobutanoic4-ChlorobutanoicacidacidacidCarbonbecomesmoreelectron-withdrawingasitsscharacterincreases:sp3

7、g(+I)Carboxylicgroupwithelectron-withdrawing(-I)Fieldeffect（场效应）:electroniceffectsistransferredbyspaceCh.P37513.3Preparationofcarboxylicacids13.3.1Preparationofcarboxylicacidsbycarboxylation（羧化作用）ofGrignardreagentGrignardreagentsreactwithcarb