130 PROCEEDINGS OF THE AMERICAN ACADEMY. 



The followiug explanation of this noteworthy decomposition of 

 sodic uitroethane is extremely probable, especially because of facts to 

 be presented later in this paper. On the addition of sodic nitroethaue, 



CH3CH = NONa, 

 II 

 O 



to a dilute acid, there is first formed the product 



CH3CH = NOH, 

 11 

 O 



which must be a strong oxidizing agent, and which therefore splits, 

 just as in analogous cases to be presented below, by intramolecular 

 oxidation into 



NOH 

 2 CH3CHO and II 



NOH. 



V. Meyer states * that on addition of an acid to aqueous sodic nitro- 

 ethane, or to a caustic alkaline solution of nitroethane, free nitroethane 

 is formed. Later he mentions f that acids never regenerate the 

 entire amount of nitroethane from a solution of this substance in 

 caustic potash, and that ethylnitrolic acid is always formed in small 

 quantity. He seems never to have noticed a decomposition into acet- 

 aldehyde and nitrous oxide, which however always takes place, as is 

 evident from the following experiments. 



20 grams nitroethane are dissolved in a solution of 20 grams caustic 

 potash (1^ molecules) in 300 c.cm. of water: the smell of nitroethane 

 is still distinctly noticeable. To this solution is added very slowly 

 dilute sulphuric acid, taking care to cool well with water. As soon 

 as the solution becomes acid, it is colored greenish, and a gas evolution 

 (N2O) and strong smell of acetaldehyde are noticed. Since no nitro- 

 ethane separates out, the sglution is extracted three times with ether. 

 The ethereal solution, after drying with calcic chloride, is then care- 

 fully fractionated; the lower boiling portions smell strongly of acetal- 

 dehyde. 7.2 grams oil were obtained, boiling between 112° and 118°, 

 which, redistilled, gave 5.2 grams, boiling between 112° and 116°. 

 The oil, although it smells of aldehyde, undoubtedly consists chiefly 



* Ann. Chera. (Liebig), CLXXI. 27-30. Cf. also Ber. d. chera. Ges., V. 

 514-516. 



t Ann. Cliem. (Liebig), CLXXV. 88-90. 



