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18.7 : Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

Nitration of benzene; chemical reaction equation; electrophilic substitution; diagram with H2SO4 catalyst.

Sulfuric acid is stronger and protonates the nitric acid on the hydroxyl group, followed by loss of water molecule, generating the nitronium ion.

Nitration reaction diagram, showing chemical reaction with nitric acid and sulfuric acid intermediates.

The nitronium ion acts as an electrophile that reacts with benzene to form a resonance-stabilized arenium ion. The arenium ion then loses its proton to a Lewis base forming nitrobenzene.

Electrophilic aromatic substitution mechanism, benzene nitration, reaction diagram, chemistry process.

The resulting nitro group can be reduced to a primary amino group. Reduction is achieved either by hydrogenation with a transition metal catalyst such as nickel, palladium, or platinum under mild conditions or upon treatment with metals in aqueous acid. Iron, zinc, and tin in dilute HCl are widely used reducing agents. However, ammonium ion is obtained as a salt under acidic conditions, which is then treated with a base such as sodium hydroxide to liberate the free amine.

Tags

Electrophilic Aromatic SubstitutionNitration Of BenzeneNitronium IonSulfuric AcidNitric AcidArenium IonNitrobenzeneReductionHydrogenationTransition Metal CatalystIronZincTinAmmonium IonPrimary Amino Group

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18.7 : Electrophilic Aromatic Substitution: Nitration of Benzene

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18.1 : Spettroscopia NMR di derivati del benzene

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18.2 : Reazioni in posizione benzilica: ossidazione e riduzione

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18.3 : Reazioni in posizione benzilica: alogenazione

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18.4 : Sostituzione Aromatica Elettrofila: Panoramica

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18.5 : Sostituzione Aromatica Elettrofila: Clorurazione e Bromurazione del Benzene

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18.6 : Sostituzione elettrofila aromatica: fluorurazione e iodinazione del benzene

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18.8 : Sostituzione elettrofila aromatica: solfonazione del benzene

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18.9 : Sostituzione aromatica elettrofila: Alchilazione del benzene di Friedel-Crafts

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18.10 : Sostituzione aromatica elettrofila: acilazione del benzene di Friedel-Crafts

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18.11 : Limitazioni delle reazioni di Friedel-Crafts

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18.12 : Effetto direttivo dei sostituenti: gruppi orto-para-direzionali

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18.13 : Effetto direzionale dei sostituenti: gruppi meta-direttivi

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18.14 : Attivatori orto-para-direzionali: –CH3, –OH, –⁠NH2, –OCH3

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18.15 : Disattivatori orto-para-direzionali: Alogeni

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