1870.] 



Hydrocarbons of the Series C n H, 



21 



and Pelouze *, but the results which I have so far obtained differ in several 

 important points from those of these eminent chemists. 



By acting on this hydrocarbon with chlorine in the cold and in presence 

 of iodine, I prepared hexyl-chloride, C G H 13 CI, already described by Cahours 

 and Pelouze, which boils at 125°-126° C. ; but besides this compound 

 there was also formed a pretty large quantity of a product which distilled 

 between 126° and 135° C, and from which no substance having a constant 

 boiling-point could be isolated. This higher boiling portion can be sepa- 

 rated only with difficulty from the chloride boiling at 125°-126°, for even 

 after repeated distillations a residue of the former is always left behind. 



On heating the lower boiling chloride with glacial acetic acid and 

 potassium acetate a hexyl-acetate was obtained, of which the larger portion 

 distilled between 158° and 162°, the boiling-point rising up at last to 170°. 

 Besides the acetate a pretty large quantity of hexylene, C 6 H 13 , had also 

 been formed by the decomposition of the chloride. 



The chloride boiling between 126° and 135°, treated in the same way, 

 yielded also hexylene, besides a hexyl-acetate distilling between 160° and 

 170°. According to Cahours and Pelouze, this ether boils at 145°. 



I did not try to isolate definite compounds from these acetates, as I 

 found that by converting them into the alcohols and subjecting these to frac- 

 tional distillation, they easily split up into two distinct compounds, — one, 

 which forms the greater part of the mixture, boiling constantly at 1 40°- 

 141°, and the other and smaller portion distilling between 150° and 155°; 

 the quantity of liquid coming over between these two limits being quite 

 insignificant. 



The liquid boiling at 140° is a secondary hexyl- alcohol '; on oxidation it 

 yields first an acetone, which, by further oxidation, splits up into acetic 

 acid and butyric acid. It is therefore methyl-bntylcarbinol, — - 



Whether this compound is identical or not with the secondary hexyl-alcohol, 

 which Erlenmeyer and Wanklyn obtained from mannite, I am not yet able 

 to decide. 



The body which distilled between 150° and 155° is & primary hexyl- 

 alcohol, C 6 II 13 OH ; on oxidizing it an oily acid was formed, which, as the 

 analysis of its silver-salt showed, has the composition of cajproic acid, 

 C 6 H 12 2 . Cahours and Pelouze mention in their memoir only the latter 

 alcohol ; they do not state, however, under what conditions they acted 

 upon the hydride with chlorine. 



I have found that, by treating this hydrocarbon with chlorine alone in 

 the cold as well as at the boiling-point, chlorides are obtained which boil 

 between 125° and 135°, and which appear to be identical with those described 

 above. I intend not only to study these chlorides more fully, but also to 



3 \ CH . OH. 



* Annal. Chim. Phys. (4) i. 5. 



