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

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⁺)).