有机化学双语版+Aldehydes+and+ketones.ppt

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1、Chapter12AldehydesandKetonesNucleophilicAdditiontoCarbonylGroup12.1Nomenclature12.2StructureofCarbonylGroup12.3Preparationofaldehydesandketones12.4Nucleophilicadditionofaldehydesandketones12.4.1Hydrationofaldehydesandketones12.4.2Theadditionofhydrogencyanide12.4.3The

2、additionofalcohols12.4.4Theadditionofamines12.5TheAdditionofYlides:theWittigReaction12.5.1Ylides(叶立德)andPreparationofphosphorousylides12.5.2MechanismoftheWittigreaction12.5.3SynthesisofalkenesbyWittigreactions12.6OxidationofAldehydesandketones12.6.1OxidationofAldehyd

3、es12.6.2Baeyer-Villigeroxidationofketones12.7SpectroscopicanalysisofaldehydesandketonesGeneralrole:Thelongestcontinuouschainwithcarbonylgroupisasaparent,suffix:ealorone.Toketones,numberedthenumberofcarbonylgroup.AldehydesandKetonesCarbonylgroup羰基Formaldehyde甲醛Aldehyd

4、e醛Ketone酮12.1NomenclatureFormyl醛基Acyl酰基Aroyl芳酰基Benzoyl芳酰基Benzylethylketone乙基苄基甲酮3-Methylbutanal3-甲基丁醛4-Methyl-3-hexanone4-甲基-3-己酮2,3-Dimethyl-4-pentenal2,3-二甲基-4-戊烯醛2.When–CHOisattachedtoaring,suffixis-aldehydeor-carbaldehyde(以甲醛为母体)Alkylgroupsareassubstitutes,“keton

5、e”areasparentBenzaldehyde苯甲醛Benzophenone二苯甲酮P2849.34-Methylcyclohexanone4-甲基环己酮12.2StructureofCarbonylGroupsp2-hybridizedπbondDipolemomentμ=2.3~2.9DTrigonalplaneABElectrondelocalizationResonancestructures:PolarsolventP283,9.2Acetaldehyde(乙醛)Acetone(丙酮)PolarizedNucleo

6、philicElectrophilicH+,E+OH-,Nu:-ReactionsitesandreactionsofaldehydesandketonesNucleophilicadditionOxidationAndreductionReactionofα-hydrogen12.4NucleophilicAdditionofAldehydesandKetonesThetrigonalplanarstructureofC=OisrelativelyopentoattackfromaboveorbelowbyNu−.:Nu:−O

7、H−,H−,R3C−,H2O,NH3,ROH:sp2sp3Intermediate:analkoxideionP2889.612.4.1HydrationofAldehydesandketonesGeminaldiol（同碳二醇）Hydrate(水合物)ReversibleK=[RCH(OH)2][RCHO][H2O]Khydr22,000411.8×10-24.1×10-32.5×10-5ReactivitydecreasesP2909.7Factorsaffectingthereactivity:1.Electronicef

8、fectsofalkylgroups2.StericeffectofalkylgroupsHybridization:sp2sp3Thebondangle:120°109.5°H