Nitration

Nitration is a chemical reaction that introduces a nitro group, –NO₂, into an organic molecule. It commonly occurs by electrophilic aromatic substitution or by radical reactions at saturated carbon atoms.

Electrophilic aromatic substitution: A reaction in which an electrophile replaces a hydrogen atom on an aromatic ring while preserving aromaticity. This is the usual pathway for nitrating electron-rich aromatic rings.
Nitrobenzene: An aromatic compound consisting of a benzene ring bonded to a nitro group. It is a major product of benzene nitration and a precursor to aniline.
Nitro group: A functional group written –NO₂, with nitrogen bonded to carbon and two oxygen atoms in organic nitro compounds. Nitration is defined by introducing this group into an organic molecule.
Sulfonation: A reaction that introduces a sulfonic acid group, –SO₃H, into an organic molecule. It is a reversible aromatic substitution that competes with nitration in some synthetic routes.
Nitric acid: A strong mineral acid and oxidizing agent with formula HNO₃. It supplies nitrogen in many nitration reactions and contributes to their corrosive hazards.
Nitronium ion: The linear cation NO₂⁺, a strong electrophile involved in many aromatic nitration reactions. It attacks the aromatic ring in the standard mixed-acid nitration mechanism.
Aniline: An aromatic amine consisting of a benzene ring bonded to an amino group. Reduction of nitrated benzene produces this widely used chemical intermediate.
Aromaticity: The unusual stability of cyclic, conjugated molecules with delocalized electrons, often described by Hückel’s rule. Aromaticity explains why substitution can occur without permanently destroying the ring’s stabilization.
Halogenation: A reaction that introduces one or more halogen atoms into a molecule. Like nitration, aromatic halogenation commonly proceeds by electrophilic aromatic substitution.
Runaway reaction: An uncontrolled acceleration of a chemical reaction caused by heat generation exceeding heat removal. Nitrations can release enough heat for poor temperature control to trigger runaway conditions.

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