1869.] Mr. C. Schorlemmer on the Derivatives of Propane. 373 



from Chancel himself. Several attempts to prepare the normal alcohol 



by synthesis failed. Thus Linnemann and Siersch* tried to obtain it by 



converting acetonitril into propylamine, by means of hydrogen in the 



nascent state, and decomposing the hydrochlorate of this base with silver 



nitrite ; but the alcohol thus formed was found to be the secondary one. 



The same compound was obtained by Butlerow and Ossokinf, by acting 



r q it 



upon ethylene iodohydrine, C 2 H 4 j j , with zinc methyl, in order to re- 

 place iodine by methyl. Now as in both cases, according to theory, the 

 normal or primary alcohol ought to have been formed, and as we have 

 no explanation why instead of this compound the secondary alcohol was 

 obtained, Butlerow and Ossokin believe that the normal propyl-alcohol 

 cannot exist. Not agreeing with this view, I was led to an investigation 

 of this subject, the results of which I have the honour to lay before the 

 Society. 



My reasoning was as follows : — It appears, as the most probable theory, 

 and which is now accepted by most chemists, that the four combining 

 powers of the carbon atom have the same value. If so, only one hydro- 

 carbon having the composition C 3 H 8 can exist. This propane must be 

 formed by replacing the iodine in the secondary propyl iodide, by hydro- 

 gen, and subjecting the hydrocarbon thus obtained to the action of chlo- 

 rine, by which primary propyl chloride must be formed in accordance with 

 the behaviour of other hydrocarbons of the same series. 



I soon found that my theory was correct ; and in a short note, which I 

 published in * Zeitschrift fiir Chemie' (1868, p. 49), I stated that I had 

 obtained the normal propyl alcohol by this method. At the same time, 

 Fittig proved that it was contained in fusel-oilst, and lately Linnemann 

 prepared it synthetically from ethyl-compounds by converting acetonitrile 

 (ethyl cyanide) into propionic anhydride, and acting upon this body with 

 nascent hydrogen§. 



The propane which I used in my researches was obtained by acting 

 upon isopropyl iodide with zinc turnings and diluted hydrochloric acid. 

 A continous evolution of gas takes place if the flask containing the mix- 

 ture is kept cold. If it is not cooled down a violent reaction soon sets in. 

 The gas always contains vapour of the iodide, even if it has been evolved 

 very slowly. In order to purify it as much as possible, it was washed 

 with Nordhausen sulphuric acid, with a mixture of nitric and sulphuric 

 acids and with caustic soda solution. 



As a gas-holder I used a tubulated bell-jar, which was suspended in a 

 larger inverted one, filled with a concentrated solution of common salt. 

 When a sufficient quantity of gas had collected, chlorine was passed into 



* Annalen Chem. Pharm. vol. cxliv. p. 137. 



t Ibid. vol. cxlv. p. 257. 



J Zeitschrift fiir Chemie, 1868, p. 44. 



§ Annalen Chem. Pharm. vol. cxlviii. p. 251. 



VOL. XVII. 2 F 



