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ID:48905057
大小:1.43 MB
页数:22页
时间:2020-02-01
《Chapter 13 Carboxylic acids.ppt》由会员上传分享,免费在线阅读,更多相关内容在行业资料-天天文库。
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:sp37、g(+I)Carboxylicgroupwithelectron-withdrawing(-I)Fieldeffect(场效应):electroniceffectsistransferredbyspaceCh.P37513.3Preparationofcarboxylicacids13.3.1Preparationofcarboxylicacidsbycarboxylation(羧化作用)ofGrignardreagentGrignardreagentsreactwithcarb
7、g(+I)Carboxylicgroupwithelectron-withdrawing(-I)Fieldeffect(场效应):electroniceffectsistransferredbyspaceCh.P37513.3Preparationofcarboxylicacids13.3.1Preparationofcarboxylicacidsbycarboxylation(羧化作用)ofGrignardreagentGrignardreagentsreactwithcarb
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