CH 16: Chemistry of Benzene. Renee Y. Becker CHM 2211 Valencia Community College. Substitution Reactions of Benzene and Its Derivatives. Benzene does not undergo electrophilic addition It undergoes electrophilic aromatic substitution maintaining the aromatic core
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Renee Y. Becker
Valencia Community College
Same mechanism as Br2 with FeBr3
Electrophile is the nitronium ion (NO2+)
Generated from HNO3 by protonation and loss of water
Fuming sulfuric acid – combination of SO3 and H2SO4
Electrophile is HSO3+ or SO3
Reaction is reversible
Favored in forward direction with strong acid
Favored in reverse direction with hot dilute aqueous acid
What product(s) would result from the nitration of each of the following compounds?