II. On the derivatives of propane (hydride of propyl)

Abstract

At the time when I commenced this investigation, the existence of normal propyl alcohol was very doubtful. According to Chancel*, this body is found in the fusel-oil from the marc of grapes ; but Mendelegeff tried in vain to isolate it from a sample of this oil which he had obtained 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 upon ethylene iodohydrine C 2 H 4 {O H I, with zinc methyl, in order to re­place 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 hydro­carbon having the composition C 3 H 8 can exist. This propane must be formed by replacing the iodine in the secondary propyl iodide, by hydro­gen, and subjecting the hydrocarbon thus obtained to the action of chlo­rine, by which primary propyl chloride must be formed in accordance with the behaviour of other hydrocarbons of the same series.