Nitrile

The grouping nitrile corresponds to - C \ equiv N. The nitriles belong to the family of derived from Carboxylic acid

Synthesis

One can very simply obtain them by nucleophilic Substitution of C \ equiv N^- on a Halogénoalcane: CN^- + X-ray \ longrightarrow R-CN + X^-

Another way of obtaining a little more complex master key by the dehydration of the corresponding Amide in the presence of a dessicant, P_4O_ {10}

Reactivity

By acid Hydrolysis (long and hot), the nitriles give a Carboxylic acid. By reduction, they give a amine and it is possible to obtain a Aldéhyde by spared reduction.

This function can have in particular an interest in the homologation (lengthening of the carbonaceous chain of an atom) of the primary amines, via the following reactions: - methylation of the primary quaternary ammonium amine - substitution by the ion cyanide and loss of trialkylamine - reduction of nitrile.

Toxicity

The nitriles are hydrolized slowly in the organization, giving the anion ^-C \ equiv N which is toxic (cyanide).

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