452 
MR. C. SOHORLEMMER ON THE NORMAL PARAFFINS. 
I have already shown that the first two of these compounds are thus formed. The 
following method seemed to me capable of determining whether the third is also 
produced. 
On heating the chlorides with an alcoholic solution of potash they are converted 
into olefines, and thus the three following hexylenes might be formed :— 
Butylethylene.CH 3 - CH, - CH, - CH, - CH=CH 3 
Metliylpropylethylene .... CH 3 —CH 3 —CH 3 —CH=CH—CH 3 
Diethyl ethylene.CH 3 - CH 3 - CH=CH - CH 3 - CH 3 
The first of these does not combine with hydrochloric acid in the cold, as Morgan 
has found, nor does the hexylene which is obtained by decomposing the secondary 
hexyl iodide from mannite, as Le Bel and Wassermann have shown. This hydro¬ 
carbon, however, is not butylethylene, as they assumed, but consists of methylpro- 
pylethylene.* 
If, therefore, normal hexane from mannite yields a hexylene combining with hydro¬ 
chloric acid in the cold, it could be only diethylethylene, which might further be 
identified by conversion into the corresponding secondary alcohol. This ought to con¬ 
sist of ethylpropyl carbinol, and should yield on oxidation only propionic acid. 
This is the programme which I intended to follow in my research ; the results 
obtained were, however, quite unexpected. 
In order to prepare pure hexane, I distilled mannite with an excess of fuming 
hydriodic acid and the addition of amorphous phosphorus. A good yield of secondary 
hexyl iodide is thus easily obtained. The iodide was reduced by the method already 
described, and the hexane separated from some hexylene and dodecane, which are 
formed at the same timed 
By the action of chlorine on the pure hydrocarbon a mixture of monochlorides, 
boiling between 121° and 134°, was obtained, which was heated with an alcoholic 
solution of potash to 100°. The reaction went on rather quickly, and was soon com¬ 
pleted. The product consisted principally of hexylene, but contained also a mixture 
of ethylhexyl ethers. 
The hexylene was left in contact with an, excess of fuming hydrochloric acid for 
several weeks, the mixture being contained in a well-closed bottle and kept in the 
dark. The excess of acid being removed, the product was, after washing and drying, 
distilled. Of course I expected to find a considerable quantity of uncombined hexy¬ 
lene to be present; but, to my great surprise, the whole product boiled constantly and 
without the least decomposition at 124—125°, while the chloride which Morgan 
obtained by the action of cold hydrochloric acid on the hexylenes from petroleum 
distilled at 116—118° with the evolution of hydrochloric acid. 
* O. Hecht, Dent. Chem. Ges. Ber., Bd. xi., p. 1152. 
t Phil. Trans., Yol. 1G2, p. 111. 
