It is also formed by heating benzoic anhydride with glycocoll (Th.
The classical investigation of Liebig and Friedrich Wihler on the radical of benzoic acid (" Uber das Radikal der Benzoesaure," Ann.
An, matter), formed the basis of benzaldehyde, benzoic acid, benzoyl chloride, benzoyl bromide and benzoyl sulphide, benzamide and benzoic ether.
However, in 1833, Berzelius reverted to his earlier opinion that oxygenated radicals were incompatible with his electrochemical theory; he regarded benzoyl as an oxide of the radical C 14 H 1Q, which he named " picramyl " (from 7rucp6s, bitter, and &uvyalk, almond), the peroxide being anhydrous benzoic acid; and he dismissed the views of Gay Lussac and Dumas that ethylene was the radical of ether, alcohol and ethyl chloride, setting up in their place the idea that ether was a suboxide of ethyl, (C2H5)20, which was analogous to K 2 0, while alcohol was an oxide of a radical C 2 H 6; thus annihilating any relation between these two compounds.
This compound is readily oxidized to benzoic acid, C 6 H 5 000H, the aromatic residue being unattacked; nitric and sulphuric acids produce nitro-toluenes, C6H4 CH3 N02j and toluene sulphonic acids, C 6 H 4 CH 3 SO 3 H; chlorination may result in the formation of derivatives substituted either in the aromatic nucleus or in the side chain; the former substitution occurs most readily, chlor-toluenes, C 6 H 4 CH 3 Cl, being formed, while the latter, which needs an elevation in temperature or other auxiliary, yields benzyl chloride, C 6 H 5 CH 2 C1, and benzal chloride, C 6 11 5 CHC1 2.