Reactions With Benzene 153z2

Reactions With Substituent Effects Electrophilic Aromatic Substitutions

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Substituent Effects of Styrenes

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Base-Catalyzed Hydrolysis of Benzoate Esters c #cc c cc c c c c

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Reactions Without Substituent Effects Nucleophilic Aromatic Substitution c *+c c cc c c c 7c c -c ccc>;ccc c -c ccc cc(

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Benzyne Reactionc c c c c*+c c c < ccc cc(

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c c c( c cc)cbut meta is major c c c cc c c c c c c c c Oxidation of Substituents on Benzene Rings -/ cc c c c(# )c c c "c 8c c cc càc@c cc c-

c c Two types of oxidationscc+ c c c À<- c

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c c KMnO< Oxidationc c c/ cc+ c c c4 c ccc c ccàc c

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c c c c c cc c/ +c ccnot oxidize × bonds of benzene ringsc c

coxidize alkene/alkynes to produce diols

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NBS Oxidationc c c/ cc+ @

cc c c ccàc c c cc c c cc+ @

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Reaction Energy Diagram

Stability of carbocation radicals •c

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Kinetic Reaction (under kinetic conditions) Major Product2c c 2 cc c c c c cc c c c c c( cο;്)c c c÷• allylic bromidec c cmajor kinetic productc( c c c c

)c c c Thermodynamic Reaction (under thermodynamic conditions) Major Product2 c c c cc

cc c c c c c1• allylic bromide c cmajor thermodynamic productcc c cc disubstituted alkenecc c Reduction of Substituents on Benzene Ringsc c Reductionc c c c c cccc càc@cc c cccc c-c c

c c Three types of reduction c # cà c& 7cà()cc c c(= cc=)c c

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c c 3?c Wolf-Kishner c &c+ c cc cc c À-àcc c c(" +)cc c c c

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