Reactions and characterisation of aromatic nitriles

Aromatic nitriles are generally liquids or low melting point solids, and usually have characteristic odours. They give no ammonia with aqueous sodium hydroxide solution in the cold, are hydrolysed by boiling aqueous alkali but more slowly than primary amides  

When distilled with soda lime (Section IV,175), nitriles yield some ammonia, but pass over, in part, unchanged. They are identified by the b.p. and by hydrolysis to, and characterisation of, the corresponding acid. 

Hydrolysis may be effected with 10-20 per cent, sodium hydroxide solution (see p-Tolunitrile and Benzonitrile in Section IV,66) or with 10 per cent, methyl alcoholic sodium hydroxide. For diflScult cases, e.g., a.-Naphthoniirile (Section IV,163), a mixture of 50 per cent, sulphuric acid and glacial acetic acid may be used. In alkahne hydrolysis the boiling is continued until no more ammonia is evolved. In acid hydro-lysis 2-3 hours boiling is usually sufficient the reaction product is poured into water, and the organic acid is separated from any unchanged nitrile or from amide by means of sodium carbonate solution. The resulting acid is identified as detailed in Section IV,175. 

Nitriles may often be hydrolysed (hydrated) to the amides (RCN— RCONHj) by concentrated sulphuric acid or by concentrated hydrochloric acid, usually in the cold or at 40° (see Sections III,115 and IV,160). The resulting amide is, of course, a useful derivative. 

The physical properties of some typical aromatic nitriles are collected in Table IV, 195. 

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