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ADVANCEDORGANICCHEMISTRYPartIIShanxiNormalUniversity2014CHAPTER7AdditiontoCarbon–HeteroMultipleBondsMECHANISMANDREACTIVITY

NucleophilicSubstitutionatanAliphaticTrigonalCarbon:

TheTetrahedralMechanism2.REACTIONS

MECHANISMS

1.1NucleophilicSubstitutionatanAliphaticTrigonalCarbon:TheTetrahedralMechanism2.REACTIONSA.AttackbyOH(AdditionofH2O)7-1TheAdditionofWatertoAldehydesandKetones:FormationofHydrates7-2HydrolysisoftheCarbon-NitrogenDoubleBond7-3HydrolysisofAliphaticNitroCompounds7-4HydrolysisofNitrilesB.AttackbyORorSR(AdditionofROH;RSH)7-5TheAdditionofAlcoholstoAldehydesandKetones7-6AcylationofAldehydesandKetones7-7ReductiveAlkylationofAlcohols7-8TheAdditionofAlcoholstoIsocyanates7-9AlcoholysisofNitriles7-10TheFormationofCarbonatesandXanthatesC.SulfurNucleophiles7-11TheAdditionofH2SandThiolstoCarbonylCompounds7-12FormationofBisulfiteAdditionProductsD.AttackbyNH2,NHR,orNR2(AdditionofNH3,RNH2,R2NH)7-13TheAdditionofAminestoAldehydesandKetones7-14TheAdditionofHydrazineDerivativestoCarbonylCompounds7-15TheFormationofOximes7-7TheConversionofAldehydestoNitriles7-17ReductiveAlkylationofAmmoniaorAmines7-18AdditionofAmidestoAldehydes7-19TheMannichReaction7-20TheAdditionofAminestoIsocyanates7-21TheAdditionofAmmoniaorAminestoNitriles7-22TheAdditionofAminestoCarbonDisulfideandCarbonDioxideE.HalogenNucleophiles7-23TheFormationofgem-DihalidesfromAldehydesandKetonesF.AttackatCarbonbyOrganometallicCompounds7-24TheAdditionofGrignardReagentsandOrganolithiumReagentstoAldehydesandKetones16-25AdditionofOtherOrganometallicstoAldehydesandKetones16-26AdditionofTrialkylallylsilanestoAldehydesandKetones16-27AdditionofConjugatedAlkenestoAldehydes(theBaylis–HillmanReaction)16-28TheReformatskyReaction16-29TheConversionofCarboxylicAcidSaltstoKetoneswithOrganometallicCompounds16-30TheAdditionofOrganometallicCompoundstoCO2andCS216-31TheAdditionofOrganometallicCompoundstoCNCompounds16-32AdditionofCarbenesandDiazoalkanestoCNCompounds16-33TheAdditionofGrignardReagentstoNitrilesandIsocyanatesG.CarbonAttackbyActiveHydrogenCompounds16-34TheAldolReaction16-35MukaiyamaAldolandRelatedReactions16-36Aldol-TypeReactionsbetweenCarboxylicAcidDerivativesandAldehydesorKetones16-37TheHenryReaction16-38TheKnoevenagelReaction16-39ThePerkinReaction16-40DarzensGlycidicEsterCondensation16-41ThePetersonAlkenylationReaction16-42TheAdditionofActiveHydrogenCompoundstoCO2andCS216-43Tollens’Reaction16-44TheWittigReaction16-45Tebbe,PetasisandAlternativeAlkenylations16-46TheFormationofEpoxidesfromAldehydesandKetones16-47TheFormationofAziridinesfromImines16-48TheFormationofEpisulfidesandEpisulfones16-49CyclopropanationofConjugatedCarbonylCompounds16-50TheThorpeReactionH.OtherCarbonorSiliconNucl

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