Electrophilic Substitution (Azo Coupling) | PraxiLabs

Electrophilic Substitution (Azo Coupling) Virtual Lab

Chemistry | Organic Chemistry

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General Aim

Diazotization of phenolic and aromatic amines. 


Azo coupling reactions are used for the diazotization of phenols and aromatic amines to produce azo dyes, and some sulfa drugs.

Learning Objectives (ILO’s)

  • <p>Become proficient at running organic chemical reactions.

  • Learning basics of organic synthesis procedures.

  • Understand the mechanism of Azo coupling reaction.

  • Learn the function of Azo coupling reaction.

  • Get trained on how the reaction is used.</p>

Theoretical Background/Context

Azo coupling reactions are a major class of organic chemical reactions that are utilized to prepare several organic molecules, especially organic dyes such as methyl orange. Azo compounds are characterized by their colors due to possessing electronically conjugated systems within their chemical structure. They have a broad range of colors that depend on the structure of each dye. 
Azo coupling reactions occur through the electrophilic attack of diazonium ions on electron rich aromatic rings containing compounds such as phenols and aromatic amines. Electrophilic diazonium ions should be freshly prepared just prior to use in azo coupling reactions as they are unstable. Moreover, their stability can be increased through their keeping in an ice bath. 
Diazonium ions can be prepared through the reaction between sodium nitrite and primary aromatic amines in the acidic medium at low temperature as shown in the below scheme.

Figure 1. Diazonium ion formation.

Principle of Work

Azo coupling reaction is carried out through diazotization of some phenolic and aromatic amines compounds such as 1-naphthol, 2-naphthol & N,N-dimethylaniline to prepare some colored dyes such as methyl orange.


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