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XII. On the Normal Paraffins .—Part III. 
By C. Schorlemmer, F.R.S., Professor of Organic Chemistry in Owens College, 
Manchester. 
Received August 2,—Read November 20, 1879. 
The isomeric monochlorides obtained from the normal paraffins existing in petroleum 
yield by the abstraction of hydrochloric acid a mixture of olefines, one portion of which 
readily combines with hydrochloric acid in the cold, whilst the other is not changed, 
even if it be left in contact with the acid for weeks, and only unites with it on 
heating.* * * § 
The chlorides which are formed in the cold boil with partial decomposition and at a 
lower temperature than the others, which distil without undergoing any change, and, 
as Morgan has shown, have the general formula, CH 3 —CHC1—C„Ho» +1 .t They are, 
therefore, derivatives of the olefines having the constitution CH 2 =CH— C ;j H 2 „ +1 or 
CH : = CHR, and which, as Le BelJ has also shown, combine with hydrochloric acid 
only on heating. 
The constitution of the olefines from petroleum which unite with the acid in the 
cold is not yet known. I have formerly pointed out that possibly they are not derived 
from normal paraffins, and this view seems to find confirmation in the observation of 
Le Bel that the property of combining with cold hydrochloric acid belongs to the 
hydrocarbons which have the general formulae CH 2 =CRB/ and CUR—CRIt'. 
On the other hand, I showed that the formation of isomeric olefines might be 
explained without making the assumption that the normal paraffins from petroleum 
contained an admixture of isomerides, but that in order to decide this question an 
absolutely pure paraffin must be used.§ 
For reasons winch are not far to seek, I selected for this investigation the normal 
hexane from mannite, which possibly might, by the action of chlorine, yield the fol¬ 
lowing monochlorides :— 
(1 ) ch 3 - ch 3 - ch 3 - ch 3 - ch 2 - CH 3 C1. 
(2 ) ch 3 -ch 3 - ch 3 - ch 3 - CHC1 - ch 3 . 
(3) CH 3 -CH 3 -CH 3 -CHC1-CH 3 -CH 3 . 
* Journ. Cliem. Soc., 1873, p. 323. 
t Ibid., 1875, p. 301. 
J Bull. Soc. Chim. (2), vol. xxviii., p. 460. 
§ Journ. Cliem. Soc., 1875, p. 306. 
