electrophilic aromatic substitution- nitrationharding/summaries/14d25.pdfelectrophilic aromatic...
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ElectrophilicAromaticSubstitution-Nitration
Sources: - Hardinger, Steven. “Chapter 23: Aromatic Substitution Reactions” OCATSA, page 31. 2012. Web -Hardinger, Steven. “Chemistry 14D: Lecture Supplement” 4th Ed. Hayden McNeil. 2016. Print
#Step1:AnAcid/BaseReaction.-protonationofthehydroxylgroupofthenitricacid
-thisprovidesabetterleavinggroup
#Step2:LeavingGroup(i.e.,water)Departure-thisformsthenitroniumion,areactiveelectrophile
#Step3:Rate-DeterminingStep*Nitroniumion(electrophile)reactswiththe
nucleophilicC=Cofthebenzeneringèratedeterminingstepbecauseitdestroys
aromaticityofthebenzene
#Step4:RegainsAromaticity*Waterfunctionsasabasetoremovetheproton
fromthenitrogroup-reformstheC=C®ainsthearomaticity
OverviewJ *Overalltransformation:Ar-HtoAr-NO2*Reagent:benzene,aq.HNO3,aq.H2SO4*Electrophilicspecies:thenitroniumion(NO2+)formedbythelossofwaterfromthenitricacid
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