'602r Prof. A. W. Hofmann on the Transformation of the [Mar. 19, 



The purification of the crude product presented no difficulty. The oil 

 was separated from the water by ether, and, after the ether had been eva- 

 porated, submitted to distillation. Between 218° and 220° the thermo- 

 meter became stationary ; the fraction distilling at that temperature solidi- 

 fied on cooling, and exhibited the boiling-point, fusing-point, and the other 

 properties of naphthaline. The thermometer then rose rapidly to 290°, and 

 the whole liquid had distilled before the thermometer reached 300°. The 

 liquid distilling between 290° and 300° was of a hght-yellow colour, and 

 of a peculiar aromatic odour ; after standing for twenty-four hours in a 

 cold room, it likewise solidified to a crystalline mass. On immersion in 

 a frigorific mixture, solidification immediately took place ; once solidified, 

 the compound no longer liquefied at the ordinary temperature. The new 

 compound thus obtained is easily soluble in alcohol ; the crystals which 

 on evaporation separate from this solution are absolutely pure. On adding 

 water to the alcoholic solution the body separates as an oil, which after a 

 few moments solidifies to a confused mass of crystals. These crystals fuse 

 at 33°-5 ; fused and resolidified, the substance is heavier than water ; its 

 boiling-point is 296°-5 (corr.). 



The new compound represents in the naphthyl-series the benzonitrile in 

 the benzoic series. Its composition, as has already been pointed out in the 

 equation exhibiting its formation, is represented by the formula 



On dissolving the nitrile in an alcoholic solution of soda, comparatively 

 little ammonia is disengaged ; but addition of water to the solution shows 

 at once that the nitrile has undergone transformation. The crystals which 

 are precipitated are far less fusible and soluble than the nitrile. By one or 

 two recrystallizations from boiling alcohol they are obtained in a state of 

 perfect purity. Thus prepared they are fine white needles, fusing at 244° 

 (corr.), and subliming at a high temperature. Analysis has proved these 

 crystals to have the composition 



C,,H,NO = C,,H,N + H,0, 



thus showing that they are the amide corresponding to the nit7'ile, from 

 which they are derived by the accession of 1 molecule of water. 



I have mentioned that the transformation of the nitrile into the amide is 

 attended by an evolution of ammonia. This evolution is obviously due 

 to the further change of the amide. Assimilating a second molecule 

 of water, this substance gives rise to the formation of an ammonium- 

 salt, 



C^.H^NO + H,0 = C,,H,,NO, = C,,H,(H,N)0„ 

 which in its turn is converted into the sodium compound vrith evolution of 

 ammonia. Indeed, on adding hydrochloric acid to the alkaline solution, an 

 abundant precipitate of a beautifully crystalline acid is obtained, the pro- 

 perties of which strongly resemble those of benzoic acid. It is scarcely 



