Nitration of Benzene

C6H6 + HNO3 → C6H5NO2 + H2O

概要

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.

参加者

役割 物質 係数 状態
反応物 Benzene C₆H₆ 1 (l)
反応物 Nitric Acid HNO₃ 1 (aq)
生成物 Water H₂O 1 (l)

日常の例

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

産業上の重要性

ニトロベンゼンは年間500万トン以上製造され、ほぼ全量がアニリンへの還元（MDI/TDI経由でポリウレタン製造）に使われる。ニトロ化は芳香族C-H官能基化の最も重要な工業反応の一つ。

特性

タイプ
Organic
可逆的
いいえ
エネルギー
発熱性
ΔH
-117.0 kJ/mol
触媒
H₂SO₄ (generates NO₂⁺)

関連する反応

Swern Oxidation Oxidation of Secondary Alcohol to Ketone Claisen Condensation (Ethyl Acetate) Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Condensation Polymerization (Nylon 6,6) Cope Rearrangement Epoxidation of Alkenes (mCPBA)

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⁺)).