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ry Principles and Mechanisms
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2nd Edition Karty
G G
Organic Chemistry: G GG
Princi ples and G G G
Mechanisms
Second Edition
G
Joel M. Karty
G G
James Wollack
G
ST.GCATHERINEGUNIVERSITY
Christopher Markworth G
WESTERNGWASHINGTONGUNIVERSITY
Jennifer Griffith G
WESTERNGWASHINGTONGUNIVERSITY
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G G G G G G G G G
2nd Edition Karty
GGGGGGGGGGGGGGGGGGGGGGGGGG G G
n W • W • NORTON & COM PANY • NEW YORK • LONDON
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CopyrightG©G2018,G2014GbyGW.GW.GNortonG&GComGpany,GIn
c.GAllGrightsGreserved.
AssociateGMediaGEditor:GArielleGHolstein
AssociateGManagingGEditor,GCollege:GCarlaGL.GTalmadge
ProductionGManGagGer:GEricGPier-GHocking
AssistantGMediaGEditor:GDorisGChiu
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G G G G G G
ry Principles and Mechanisms
G G G
2nd Edition Karty
G G
CONTENTS
G PrefaceG
G v
G ChapterG1G|GAtomicGandGMolecularGStructureG 1
InterchapterGAG|GNomenclature:GTheGBasicGSystemGforGNamingGSGimpleGOrganicGG
Compounds—GAlkanes,GHaloalkanes,GNitroalkanes,GCycloalkanes,GG
andGEthersG 35
G ChapterG2G|GThree-GDimensionalGGeometry,GIntermolecularGInteractions,GandGG
PhysicalGPropertiesG 47
G ChapterG3G|GOrbitalGInteractionsG1:GHybridizationGandGTwo-GCenterGMolecularGOrbitalsG 75
G InterchapterGBG|GNamingGAlkenes,GAlkynes,GandGBenzeneGDerivativesG 103
G ChapterG4G|GIsomerismG1:GConformersGandGConstitutionalGIsomersG 114
G ChapterG5G|GIsomerismG2:GChirality,GEnantiomers,GandGDiastereomersG 143
G InterchapterGCG|GStereochemistryGinGNomenclature:GRGandGSGConfigurationsGaboutGG
AsymmetricGCarbonsGandGZGandGEGConfigurationsGaboutGDoubleGBondsG 172
G ChapterG6G|GTheGProtonGTransferGReaction:GAnGIntroductionGtoGMechanisms,GG
Thermodynamics,GandGChargeGStabilityG 184
G ChapterG7G|GAnGOverviewGofGtheGMostGCommonGElementaryGStepsG 211
G InterchapterGDG|GMolecularGOrbitalGTheory,GHyperconjugation,GandGChemicalGReactionsG 243
G InterchapterGEG|GNamingGCompoundsGwithGaGFunctionalGGroupGThatGCallsGforGaGG
SuffixG1:GAlcohols,GAmines,GKetones,GandGAldehydesG 254
G ChapterG8G|GAnGIntroductionGtoGMultistepGMechanisms:GSN1GandGE1GReactionsGandGG
TheirGComparisonsGtoGSN2GandGE2GReactionsG 265
G ChapterG9G|GNucleophilicGSubstitutionGandGEliminationGReactionsG1:GCompetitionGG
amongGSN2,GSN1,GE2,GandGE1GReactionsG 292
G InterchapterGFG|GNamingGCompoundsGwithGaGFunctionalGGroupGThatGCallsGforGaGG
SuffixG2:GCarboxylicGAcidsGandGTheirGDerivativesG 320
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G G G G G G G G G
2nd Edition Karty
GGGGGGGGGGGGGGGGGGGGGGGGGG G G
G ChapterG10G|GNucleophilicGSubstitutionGandGEliminationGReactionsG2:GReactionsGG
ThatGAreGUsefulGforGSynthesisG 331
G ChapterG11G|GElectrophilicGAdditionGtoGNonpolarGπGBondsG1:GAdditionGofGaGBrønstedGG
AcidG 361
G ChapterG12G|GElectrophilicGAdditionGtoGNonpolarGπGBondsG2:GReactionsGInvolvingGG
CyclicGTransitionGStatesG 388
G ChapterG13G|GOrganicGSynthesisG1:GBeginningGConceptsGinGDesigningGMultistepGSynthesisG 415
G ChapterG14G|GOrbitalGInteractionsG2:GExtendedGπGSystems,GConjugation,GandGAromaticityG 445
GChapterG15G|GStructureGDeterminationG1:GUltraviolet–GVisGiGbleGandGInfraredGSpectroscopiesG 469
G ChapterG16G|GStructureGDeterminationG2:GNuclearGMagneticGResonanceGSpectroscopyGG
andGMassGSpectrometryG 500
G ChapterG17G|GNucleophilicGAdditionGtoGPolarGπGBondsG1:GAdditionGofGStrongGNucleophilesG 533
G ChapterG18G|GNucleophilicGAdditionGtoGPolarGπGBondsG2:GWeakGNucleophilesGandGAcidGG
andGBaseGCatalysisG 567
G ChapterG19G|GOrganicGSynthesisG2:GIntermediateGTopicsGinGSynthesisGDesign,GandGG
UsefulGRedoxGandGCarbon–GCarbonGBond-GFormingGReactionsGG 606
ChapterG20G|GNucleophilicGAddition–GEliminationGReactionsG1:GTheGGeneralGG
MechanismGInvolvingGStrongGNucleophilesG 645
G ChapterG21G|GNucleophilicGAddition–GEliminationGReactionsG2:GWeakGNucleophilesG 681
G ChapterG22G|GAromaticGSubstitutionG1:GElectrophilicGAromaticGSubstitutionGonGG
Benzene;GUsefulGAccompanyingGReactionsG 723
G ChapterG23G|GAromaticGSubstitutionG2:GReactionsGofGSubstitutedGBenzenesGandGOtherGRingsG 752
G ChapterG24G|GTheGDiels–GAlderGReactionGandGOtherGPericyclicGReactionsG 790
G ChapterG25G|GReactionsGInvolvingGGFreeGRadicalsG 826
G InterchapterGGG|GFragmentationGPathwaysGinGMassGSpectrometryG 856
G ChapterG26G|GPolymersG 876
G CreditsG
G 902
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