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Electrophilic Aromatic Substitution: Nitration of Benzene

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.

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

meta-Directing Deactivators: –NO₂, –CN, –CHO, –⁠CO₂R, –COR, –CO₂H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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Related Experiment Video

Updated: Jun 5, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Published on: February 10, 2023

2,4-Dichloro-6-nitro-benzoic acid.

Hai-Lian Liu¹, Zhi-Qiang Du

¹Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

Researchers synthesized a novel compound, C(7)H(3)Cl(2)NO(4), using 2,4-dichloro-6-nitro-toluene and nitric acid. The study details its unique molecular structure and crystal stabilization through hydrogen bonding.

Area of Science:

Organic Chemistry
Crystallography

Background:

The synthesis of novel organic compounds is crucial for developing new materials and pharmaceuticals.
Understanding the structural properties of synthesized molecules provides insights into their potential applications.

Purpose of the Study:

To synthesize and characterize a new chemical compound, C(7)H(3)Cl(2)NO(4).
To elucidate the molecular structure and crystal packing of the synthesized compound.

Main Methods:

Chemical synthesis involving the reaction of 2,4-dichloro-6-nitro-toluene with nitric acid at 430 K.
X-ray crystallography to determine the crystal structure and molecular geometry.

Main Results:

The compound C(7)H(3)Cl(2)NO(4) was successfully synthesized.

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The carboxyl and nitro groups exhibit significant twisting (82.82° and 11.9°, respectively) relative to the benzene ring.

Crystal structure is stabilized by intermolecular O-H⋯O and C-H⋯O hydrogen bonds.

Conclusions:

The study successfully synthesized and characterized a novel compound with a unique structural configuration.
The identified hydrogen bonding interactions are key to the crystal lattice stability.