chapter 13 nmr spectroscopy：13章核磁共振光谱

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1、Chapter15:ReactionsofSubstitutedBenzenesLearningObjectives:1.Beabletorecognizeandutilizetheoxidativeandreductivereactionsinvolvingthesubstituentsonbenzene.2.Recognizewhetherasubstituentonabenzeneringisactivatingordeactivatingtowardelectrophilicaromaticsubstitutionreac

2、tion,andwhyitisso.3.Predicttheeffectasubstituentwillhaveontheregioselectivityofanelectrophilicsubstitutionreaction.4.PredicttheeffectasubstituentwillhaveonpKa.5.Beabletodesignthesynthesisofamultisubstitutedbenzene.6.Beabletorecognizeandutilizethereactionsinvolvingaren

3、ediazoniumsalts.7.Recognizeandbeabletowritethemechanismofnucleophilicaromaticsubstitution.8.Recognizethestructureofbenzyne,beabletoexplainhowitisformed,andhowitreacts.Sections:15.1NomenclatureofDisubstitutedandPolysubstitutedBenzenes15.2SomeSubstituentsIncreasetheReac

4、tivityofaBenzeneRingandSomeDecreaseItsReactivity*15.3TheEffectofSubstituentsonOrientation(Regioselectivity)*15.4TheEffectSubstituentonpKa15.5TheOrtho-Pararatio15.6AdditionalConsiderationsRegardingSubstituentEffects15.7DesigningaSynthesisIII:Synthesisofmonosubstituteda

5、ndDisubstitutedBenzenes*15.8SynthesisofTrisubstitutedBenzenes15.9SynthesisofSubstitutedBenzenesUsingArenediazoniumSalts*15.10TheArenediazoniumIonasanElectrophile*15.11MechanismfortheReactionofAmineswithNitrousAcid*15.12NucleophilicAromaticSubstitutionReactions:AnAddit

6、ion-EliminationMechanism*15.13NucleophilicAromaticSubstitutionReactions:AnElimination-AdditionMechanismThatFormsaBenzyneIntermediate15.14PolycyclicBenzenoidHydrocarbons#*Sectionsthatwillbefocused#SectionsthatwillbeskippedRecommendedadditionalproblems15.34–15.6921Class

7、Note15.1NomenclatureofDisubstitutedandPolysubstitutedBenzenes2115.2SomeSubstituentsIncreasetheReactivityofaBenzeneRingandSomeDecreaseItsReactivity*and15.3TheEffectofSubstituentsonOrientation(Regioselectivity)*A.RelativerateofelectrophilicaromaticsubstitutionExamples:·

8、Rate-determiningstep(r.d.s)·Resonanceeffectandinductiveeffect21B.RelativereactivityandregioselectivityofsubstitutedbenzenesS