Nitration of Benzene

C6H6 + HNO3 → C6H5NO2 + H2O

Aperçu

Benzene undergoes electrophilic aromatic substitution with nitric acid in the presence of sulfuric acid to form nitrobenzene. The active electrophile is the nitronium ion (NO₂⁺) generated by protonation of HNO₃. The reaction temperature must be carefully controlled to avoid dinitration.

Participants

Rôle Substance Coefficient État
Réactif Benzene C₆H₆ 1 (l)
Réactif Nitric Acid HNO₃ 1 (aq)
Produit Water H₂O 1 (l)

Exemple du quotidien

Nitrobenzene has a bitter almond odor and was once used in shoe polish and floor wax. TNT is made by trinitration of toluene.

Importance industrielle

Nitrobenzene is produced at over 5 million tonnes annually, almost entirely for reduction to aniline, the precursor to polyurethanes and dyes.

Propriétés

Type
Organic
Réversible
Non
Énergie
Exothermique
ΔH
-117,0 kJ/mol
Catalyseur
H₂SO₄ (generates NO₂⁺)

Réactions associées

Epoxidation of Alkenes (mCPBA) Swern Oxidation Oxidation of Secondary Alcohol to Ketone E2 Elimination (Dehydrohalogenation) Claisen Condensation (Ethyl Acetate) Aldol Condensation of Acetaldehyde Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Dehydration of Ethanol

Frequently Asked Questions

What is the equation for Nitration of Benzene?
The balanced equation is: C₆H₆ + HNO₃ → C₆H₅NO₂ + H₂O.
What type of reaction is Nitration of Benzene?
Nitration of Benzene is a organic reaction.
Is Nitration of Benzene exothermic or endothermic?
Nitration of Benzene is exothermic (releases energy). The enthalpy change (ΔH) is -117.0 kJ/mol.
What conditions are needed for Nitration of Benzene?
This reaction requires a catalyst (H₂SO₄ (generates NO₂⁺)).