NEP. — BIVALENT CARBON. 157 



CHfiN : CCl 

 I 

 CII3CO, 



into its components must take place on distillation, and an analysis of 

 the substance would therefore be of no value. One encounters here, 

 as has also been observed in the case of many other addition products 

 of the isocyanides,* the remarkable property that these are easily 

 split into their components, either at higher temperatures, or on stand- 

 ing in the cold, or on treatment with sodic hydrate ; whereas, on the 

 other hand, these components either at — 20° or at ordinary or higher 

 temperatures often unite with explosive violence. Bivalent carbon 

 therefore behaves exactly like trivalent nitrogen in ammonia and the 

 amines, since also the last named compounds unite often with explosive 

 violence with acids, e. g. hydrochloric acid, forming addition products 

 containing quinquivalent nitrogen, which in turn, either by heating or 

 by treating with alkalies, are split into their components. 



That the above distilled oil a , however, still contains much ethyl- 

 iraidopyruvylchloride, is shown by decomposing it with water: it is 

 converted thereby into pyruvic-ethylamide, 



C^HgN : COH 

 I 

 CH3CO, 



the presence of which in the aqueous solution, since it cannot be ex- 

 tracted therefrom by ether, is best shown by adding phenylhydrazine- 

 hydrochloride, which precipitates an insoluble hydrazone (3.5 grams). 

 The above mentioned portion b was not distilled, but decomposed 

 directly with ice water, and the reddish-colored solution treated with 

 phenylhydrazinehydrochloride, and thus 7.7 grams insoluble hydrazone 

 were obtained. The hydrazone is obtained, when recrystallized from 

 alcohol, in colorless many-sided heavy crystals, melting at 165°. It 

 is insoluble in alkalies and in water. 



0.2002 gram substance, dried at 100°, gave 0.4731 gram CO2 and 



0.1387 gram H^O. 

 0.1494 gram substance, dried at 100°, gave 27.5 c.cm. Ng at 20° and 



747 mm. 



* Ann. Chem. (Liebig), CCLXX. 297, 298, 322. 



