PrefacetotheStudent
PrefacetotheInstructor
1TheBasics
1.1StructureandStabilityofOrganicCompounds
1.1.1ConventionsofDrawingStructures;Grossman’SRule
1.1.2LewisStructures;ResonanceStructures
1.1.3MolecularShape;Hybridization
1.1.4Aromaticity
1.2BrCnstedAcidityandBasicity
1.2.1PKValues
1.2.2Tautomerism
1.3KineticsandThermodynamics
1.4GettingStartedinDrawingaMechanism
1.5ClassesofOverallTransformations
1.6ClassesofMechanisms
1.6.1PolarMechanisms
1.6.2Free.RadicalMechanisms
1.6.3PericyclicMechanisms
1.6.4Transition-Metal-Catalyzedand-MediatedMechanisms
1.7Summary
Problems
2PolarReactionsunderBasicConditions
2.1SubstitutionandEliminationatC(sp3)一XBonds.PartI
2.1.1SubstitutionbytheSN2Mechanism
2.1.2EliminationbytheE2andElcbMechanisms
2.1.3PredictingSubstitutionVS.Elimination
2.2AdditionofNucleophilestoElectrophilic仃Bonds
2.2.1AdditiontoCarbonylCompounds
2.2.2ConjugateAddition;TheMichaelReaction
2.3SubstitutionatC(sp2)一XBouds
2.3.1SubstitutionatCarbonylC
2.3.2SubstitutionatAlkenylandArylC
2.3.3MetalInsertion;Halogen-MetalExchange
2.4SubstitutionandEliminationatC(sp3)-XBonds,PartII
2.4.1SubstitutionbytheSRNlMechanism
2.4.2SubstitutionbytheElimination-AdditionMechanism
2.4.3SubstitutionbytheOne-ElectronTransferMechanism
2.4.4MetalInsertion;Halogen一MetalExchange
2.4.5Ol-Elimination;GenerationandReactionsofCarbenes
2.5Base-PromotedRearrangements
2.5.1MigrationfromCtoC
2.5.2MigrationfromCtoOorN
2.5.3MigrationfromBtoCorO
2.6TwoMultistepReactions
2.6.1TheSwemOxidation
2.6.2TheMitsunobuReaction
2.7Summary
Problems
3PolarReactionsUnderAcidicConditions
3.1Carbocations
3.1.1CarbOCationStability
3.1.2CarbocationGeneration;TheRoleofProtonation
3.1.3TypicalReactionsofCarbocations;Rearrangements
3.2Substitutionand一EliminationReactionsatC(sp3)一X
3.2.1SubstitutionbytheSNlandSN2Mechanisms
3.2.2EliminationbytheE1Mechanism
3.2.3PredictingSubstitutionVS.Elimination
3.3ElectrophilicAdditiontoNucleophilicC=CBonds
3.4SubstitutionatNucleophilicC=CBonds
3.4.1ElectrophilicAromaticSubstitution
3.4.2AromaticSubstitutionofAnilinesviaDiazoniumSalts
3.4.3ElectrophilicAliphaticSubstitution
3.5NucleophilicAdditiontoandSubstitutionatElectrophilicBonds
3.5.1HeteroatomNucleophiles
3.5.2CarbonNucleophiles
3.6Summary
Problems
4PericyclicReactions
4.1Introduction
4.1.1ClassesofPericyclicReactions
4.1.2PolyeneMOs
……
5Free.RadicalReactions
6Transition-Metal-Mediatedand-Cata!vzedReactions
7Mixed.MechanismProbiems
AF.nalWord
Index