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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.

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...

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

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...

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.

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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

2-Nitro-benzyl 2-chloro-acetate.

Kai Zhu¹, Hui Liu, Yan-Hua Wang

¹College of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals intramolecular hydrogen bonding in a chlorinated nitroaromatic compound, forming a near-planar ring. Intermolecular interactions further organize these molecules into a 2D crystal network.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

Area of Science:

Crystal engineering
Supramolecular chemistry
Organic chemistry

Background:

Understanding molecular interactions is crucial for designing novel materials.
Intramolecular hydrogen bonds influence molecular conformation and properties.
Crystal packing dictates bulk material characteristics.

Purpose of the Study:

To investigate the structural features and intermolecular interactions of a specific chlorinated nitroaromatic compound.
To elucidate the role of intramolecular C-H⋯O interactions in ring formation.
To characterize the crystal structure and network formation.

Main Methods:

Single-crystal X-ray diffraction analysis.
Analysis of intramolecular and intermolecular hydrogen bonding.
Conformational analysis of the molecule.

Main Results:

The title compound, C(9)H(8)ClNO(4), exhibits an intramolecular C-H⋯O interaction forming a near-planar five-membered ring.
This ring is oriented at a dihedral angle of 4.07° relative to the adjacent aromatic ring.
Intermolecular C-H⋯O interactions facilitate the assembly of molecules into a two-dimensional network in the crystal structure.

Conclusions:

The presence of intramolecular C-H⋯O interactions significantly influences the molecular geometry.
The observed crystal packing highlights the role of weak interactions in constructing extended supramolecular architectures.
This study contributes to the understanding of structure-property relationships in organic crystalline materials.