Aliphatic diazonium salts are unstable Why

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Area of ‚Äč‚ÄčExpertise - Organic chemistry

Diazotization is the term used to describe the production of diazonium salts () by reacting primary, aromatic amines () with cold, dilute nitrous acid.

General reaction equation:

In the case of the primary aliphatic (open-chain) amines, diazotization can also be carried out. The diazonium ions formed become very unstable and change into carbenium ions with the elimination of nitrogen.

The diazonium salts formed are important intermediate stages in further organic syntheses, for example in the preparation of azo dyes by azo coupling, in the Sandmeyer reaction (conversion of aryldiazonium salts to aryl cyanide or aryl halides) and in the Schiemann reaction.

Learning units in which the term is dealt with

Aromatic reactions (total)90 min.

chemistryOrganic chemistryAromatic chemistry

This learning unit begins with a description of the mechanism of electrophilic aromatic substitution, including energetic considerations of the intermediates and transition states. Furthermore, the dependencies between inductive and mesomeric effects and the reactivity and the secondary substitution of substituted aromatics are dealt with. The most important reactions are also presented. Finally, the less important nucleophilic aromatic substitution is explained, including the mechanism, intermediates, transition states, etc., etc. The conclusion is a description of the "production" and structure of arynes.

Aromatic reactions - examples of the Ar-SE reaction30 min.

chemistryOrganic chemistryAromatic chemistry

This learning unit covers the most important examples of electrophilic aromatic substitution. These include nitration, sulfonation, halogenation, Friedel-Crafts alkylation, Friedel-Crafts acylation, diazotization and azo coupling.