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&regainsthearomaticity

OverviewJ *Overalltransformation:Ar-HtoAr-NO2*Reagent:benzene,aq.HNO3,aq.H2SO4*Electrophilicspecies:thenitroniumion(NO2+)formedbythelossofwaterfromthenitricacid