270 
MESSRS. C. SCHORLEMMER AND T. E. THORPE 
The results of the oxidation show therefore that primary heptyl alcohol and methvl- 
pentyl-carbinol had been formed, as in the case of heptane from petroleum. 
Another portion of the mixture of the monochlorides was then heated to 100° with 
alcoholic solution of potash, whereby in addition to heptylene a mixture of the ethyl 
heptyl ethers was obtained. The heptylene, purified by repeated rectification over 
sodium, boiled constantly at 98 0, 5. It was placed in contact with an excess of fuming 
hydrochloric acid in the dark and in a well-closed bottle for six weeks. Heptylene 
from petroleum heptane was similarly treated. 
Now it is remarkable that whilst hexylene from mannite combines completely with 
hydrochloric acid under these circumstances forming secondary hexyl chloride (Phil. 
Trans., 1880, p. 457), the greater part of the heptylene from Pinus heptane was found 
to be unattacked, not more than 10 per cent, of heptyl chloride having been formed. 
On the other hand, about one-half of the heptylene from petroleum had been converted 
into the chloride in accordance with the former observations made by one of us on this 
point. 
The uncombined portions of both specimens of heptylene were again placed in con¬ 
tact with the fuming acid, and (the research being interrupted by other work) they 
were allowed so to remain for many months. At the expiration of this time it was 
found that the Pinus heptylene had united almost completely with the acid, whilst 
an additional quantity of the heptylene from petroleum had likewise entered into 
combination. It follows from this that, contrary to expectation, hydrochloric acid 
acting in the cold is not capable of effecting the separation of isomeric paraffins (Phil. 
Trans., 1880, p. 451). 
It is remarkable that the Pinus heptylene should require so long a time to bring 
about its union with hydrochloric acid, since, as will be shown immediately, its con¬ 
stitution is exactly analogous to that of the hexylene from mannite or propyl-methyl 
ethylene, C 3 H 7 .CH = CH.CH 3 , which so easily goes into combination. 
In order to establish the constitution of the heptylene from Pinus it was oxidised 
by means of a solution of potassium dichromate in dilute sulphuric acid in the manner 
adopted by Hecht in the oxidation of hexylene from mannite (Ber. Deutsch. Chem. 
Ges., Bel. xi., S. 1152). The acids so formed were converted into the silver salts and 
analysed with the following results : — 
Fraction. 
Salt taken. 
Silver found. 
Silver pentoate 51'67 
1 
0-0855 
0-0443 
51-81 
2 
0-0560 
0-02875 
51-34 
Q 
o 
0-1140 
0-0590 
51-75 
4 
0-1350 
0-0700 
51-84 
5 
0-0685 
0-0350 
51-09 
6 
o-iooo 
0-0540 
54-00 
7 
0-2200 
0-1370 
62-27 
8 
0-1370 
0-0855 
6 4" 6 0 
9 
0-1400 
0-0910 
65-00 
Silver acetate 64'67. 
