154 PROCEEDINGS OF THE AMERICAN ACADEMY. 



purification used by Elbers * does not yield an absolutely pure product; 

 it is much better to recrystallize from benzene, wherein the substance 

 is readily soluble on heating, but practically insoluble in the cold. 

 Yellow needles melting at 163° (Elbers gives mpt. 153°) were thus 

 obtained. 



0.1661 gram substance, dried at 90°, gave 0.4259 gram COg and 



0.0750 gram HgO. 

 0.1008 gram substance, dried at 90°, gave 11 c.cm. Ng at 25° and 



739 mm. 



Theory for CuHijNjOj- Found. 



C 70.00 69.93 



H 5.00 5.02 



N 11.66 11.82 



Molecular Rearrangement of Etiiylisocyanide to Propionitrile. 



Ethylisocyanide was made according to the method of Gautier,t by 

 heating 100 grams silvercyanide and 115 grams ethyliodide for one 

 and one half hours on a water bath (with reversed condenser and 

 with a mercury valve). The substance (bpt. 79°) can be kept for 

 fifteen months without the slightest change. It can be heated without 

 any essential change for many hours to 210° ; a slight yellow colora- 

 tion only is noticed, t The first statements of Gautier § concerning 

 this substance, which he does not mention in his later paper, || are 

 therefore to be corrected. On heating ethylisocyanide, however, to 

 a still higher temperature, molecular rearrangement to ethylcyanide 

 takes place almost quantitatively. 7.5 c.cm. ethylisocyanide are 

 heated in a sealed tube for three hours between 230°-255°, and the 

 contents of the tube, which are colored brown and smell slightly of 

 ammonia and isocyanide, distilled off. Everything came over except 

 a slight residue between 94° and 98°. In order to remove ammonia 

 and traces of isonitrile, the oil was washed with a chloride of calcium 

 solution containing hydrochloric acid, and then dried with solid calcic 

 chloride. On distilling, a pleasant ethereal smelling oil, boiling con- 

 stant at 97°, was obtained (4 c.cm.), which was identical in every 

 respect with propionitrile. 



0.1528 gram substance gave 0.3608 gram COg and 0.1278 gram HgO. 

 0.1530 gram substance gave 33.5 c.cm. Ng at 9° and 741 mm. 



* Ann Chem. (Liebig), CCXXVII. 341. 



t Lor. r,i , [4.], XVII. 233. § Loc. at., [4.], XVII. 236. 



t Comptcs Rendus, LXV. 862. || Ibid., 203-260. 



