126 PROCEEDINGS OF THE AMERICAN ACADEMY. 



it is very well possible * that on treating it with sodic hydrate or with 

 sodium ethylate, an addition of these reagents to the nitro group takes 

 place, forming thus the products, 



CH3-CH,-N^^^ and CHa-CH^-N^^^^a' 

 O O 



which by loss of water or alcohol must give sodic nitroethane of the 



constitution 



CH3CH = NONa. 



II 

 O 



This reaction is entirely analogous to the formation of sodic malonic 

 ether from malonic ether and sodium ethylate,t the only difference 

 being in the fact that sodic malonic ether is instantly decomposed by 

 water, regenerating the ester and forming sodic hydrate,! whereas 

 sodic nitroethane dissolves in water without decomposition. 



In favor of this interpretation of salt formation can be adduced the 

 fact that many higher members of the nitroparaflSne series, which 

 ought, like nitroethane, to possess acid properties, dissolve only with 

 great difficulty and on prolonged treatment in very concentrated sodic 

 hydrate ; § i. e. they possess very weak acid properties and were con- 

 sequently long considered to be neutral substances, || — a fact which, 

 as V. Meyer also observes,1[ is very noteworthy. If, however, the 

 salt formation depends on the addition of sodic hydrate to the nitro 

 group and subsequent loss of water, the peculiar and unexpected 

 behavior observed in these cases is easily comprehensible ; the first 

 members of the nitroparaffine series are soluble in water, and thus 

 more easily attacked by sodic hydrate, whereas the higher members 

 are insoluble in water. 



Since, according to this conception of the nitroparaffine salts, they 

 do not possess a constitution analogous to that of the free nitro com- 

 pounds, it does not of necessity follow, especially since the salts are 

 soluble without decomposition in water, that these salts can be con- 



* These Proceedings, XXVII. 150-158. 

 t Ann. Chem. (Liebig), CCLXVI. 67, CCLXXVI. 244. 

 t Ibid., CCLXVI. 113. 



§ Ibid., CLXXV. 135, 144; Ziiblin,Ber. d. chem. Ges., X. 2083; Konowalow, 

 Ber. d. chem. Ges., XXV. Ref. 108. 



II Ber. d. chem. Ges., V. 203; Ann. Chem. (Liebig), CLXXI. 44. 

 1[ Lehrbuch, p. 205. 



