364 Prof. C. Schorl emrner on the Normal Paraffins. [Nov. 20 y 



XL " On the Normal Paraffins. Part III." By 0. Schorlemmer, 

 F.R.S., Professor of Organic Chemistry in Owens College, 

 Manchester. Received August 2, 1879. 



(Abstract.) 



The isomeric monochlorides, obtained from the normal paraffins exist- 

 ing* in petroleum, yield by the abstraction of hydrochloric acid a 

 mixture of olefines, one portion of which readily combines with hydro- 

 chloric acid in the cold, whilst the other unites with it only on 

 'heating.* 



The chlorides formed in the cold boil with partial decomposition 

 and at a lower temperature than the others, which distil without 

 undergoing any change, and have the general formula 



CH 3 — CHC1— C,H 2 , +1 .f 



They are therefore derived from the olefines of the series 



CH 2 zz CH — C W H 2H+1 . 



Similar results have been obtained by Le Bel.lf 



The constitution of the olefines combining with the acid in the cold 

 is not yet known. They are possibly not derived from normal 

 paraffins, but from isomerides, which cannot be separated from the 

 former by distillation. On the other hand their formation can also 

 be explained without making this assumption. This question can 

 only be decided by using an absolutely pure paraffin. § 



For this purpose, normal hexane from mannite was selected, which 

 possibly might yield three isomeric monochlorides : 



(1.) CH 3 — CH,— CH,— CHo— CHo— CHoCl 

 (2.) CH 3 — CHo— CHo— CH~— CHC1— CH 3 

 (3.) CHo — CH 2 — CHo — CHC1 — CH 2 — CH 3 



The formation of the first two has already been proved. || The- 

 following seemed capable of determining whether the third is also 

 produced. By the abstraction of hydrochloric acid three hexylenes 

 might be formed : — 



Butylethylene . . . . CH 3 — CH 2 — CH 2 — CH 2 — CH=CH 2 

 Methylpropylethylene . . CH 3 — CH 2 — CHo— CH=CH— CH 3 

 Diethylethylene .. .. CH 3 — CH 2 — CHzzCH— CH 2 — CH 3 



The first of these does not combine with cold hydrochloric acid ; 

 the second is the hexylene obtained from secondary hexyl iodide. || 



* " Journ. Chein. Soc," 1873, p. 319. 



t Morgan, ibid., 1875, p. 301. 



+ "Bull. Soc. Chira.," (2), xxviii, p. 460. 



§ "Journ. Chem. Soc," 1875, p. 306. 



|| Hecht, "Deut. Chem. Ges. Ber.," si, p. 1152. 



