NEF. — NITROPARAFFINE SALTS. 127 



verted back again completely into the free nitro bodies from which 

 they were obtained. The first problem therefore was to determine 

 this point by experiment, and it was found that under no condition is 

 it possible to convert these salts back again completely into the cor- 

 responding free nitro compounds. On adding an aqueous solution 

 of a sodium salt of a nitroparalfine to cold dilute sulphuric or 

 hydrochloric acid, not a trace of the nitroalkyle is regenerated, 

 but a more or less smooth decomposition into nitrous oxide and an 

 aldehyde or ketone takes place, according to one of the following 

 equations : 



I. 2 R-CH = NONa + 2 HCl 



O 



Sodium Salt of a Primary Nitroparafflne. 



N^ / NOHv 



= 2 R-CH : O + II O from II +2 NaCL 



N'^ V NO 11/ 



11. 2 ^^C = NONa + 2 HCl 

 R/ II 



O 



Sodium Salt of a Secondary NitroparaflSne. 



R\ N^ / NOHx 



= 2 ;C:0+ll O ( from II ) + 2 NaCl. 



R/ N^ \ NOH/ 



This new very noteworthy decomposition of nitroparaffine salts, 

 which always takes place, no matter how the experiment is carried 

 out, has been overlooked by V. Meyer and by all who have worked 

 with these compounds. V. Meyer states repeatedly that it is possible 

 to regenerate the free nitroparaffine from its sodium salt or from a 

 caustic alkaline solution, — a fact which is only true to a limited ex- 

 tent (see below). Decomposition always takes place according to one 

 or the other of the above equations, and this fact alone proves that the 

 nitroparaffine salts cannot possibly have a constitution analogous to 

 that of the free nitroalkyles. 



If, for example, sodic nitroethane possessed the constitution 



CHgCHNa 



I 

 NO,, 



it ought to be possible to convert it quantitatively into CH,— CHoNO.j 

 by addition to dilute sulphuric acid, just as sodium acetate goes over 



