nitration
An important process in organic chemistry,
in which a nitro group (–NO2) is introduced into a compound.
Aromatic compounds are nitrated
with a mixture of concentrated sulfuric
acid and nitric acid, which contains
the electrophile; the production of
TNT and nitrobenzene are important cases. "Nitration" is a term also used
to describe the formation of nitrate esters
including nitrocellulose and nitroglycerin.
Illustrated to the right is the nitration of benzene,
which produces a reaction that goes through several stages. Initially (A),
the entering group approaches and associates weakly with the benzene ring
(B). Then, rearrangement produces an unstable high-energy intermediate (C),
which breaks down to a complx (D) in which the leaving group is weakly associated
with the ring. It ends with the departure of the leaving group (E).
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