46 
THE PHARMACEUTICAL JOURNAL AND TRANSACTIONS. 
[July 20, 1872. 
The constitution of these olefines has been fully proved 
by experiment. On combining them with hydriodic 
acid, secondary iodides are formed, which, when con¬ 
verted into alcohols, yield acetones, containing the 
group methyl, as an oxidation they yield acetic acid, be¬ 
sides another fatty acid. Now Popoflf has established 
the law that when an acetone is oxidized, the more 
simple alcohol-radical always remains combined with 
the group carbonyl, whilst the other is oxidized by 
itself, yielding a fatty acid containing the same number 
of carbon atoms as the alcohol-radical itself (Ann. Chew. 
I*harm., cxlv. 283, and clxi. 285). Thus when hexylene, 
obtained from mannite, is subjected to the above reac¬ 
tions, we obtain acetic acid and butyric acid:— 
Hexylene, 
or butyl- 
«thene. 
Secondary 
hexyl- 
iodide. 
Secondary 
hexyl- 
alcohol. 
Methyl- 
hutyl- 
ketone. 
C 4 H 9 
CH 
11 
c 4 h 9 
c 4 h 9 
c 4 h 9 
CHI 
1 
1 
CH.OH 
1 
CO 
II 
ch 2 
ch 3 
| 
ch 3 
1 
ch 3 
Butyric 
acid. 
c 4 h 10 o 2 
Acetic Acid. 
CO.OH 
Besides these olefines, Butlerow has lately described 
some in which carbon atoms situated in the middle of 
Hm chain are linked together by two units. The consti¬ 
tution of these bodies, which were obtained from tertiary 
compounds, is easily. understood, as the constitution of 
the alcohols from which they have been derived is well 
known. Thus, on acting with alcoholic potash on the 
iodide of triethyl-carbinol, CI(C 2 H 5 ) 3 , a pseudohepty- 
lene is obtained, having the following constitution 
ch 3 - ch 2 —c—ch 2 —ch 3 
CH 
ever, appears improbable, as diamylene is so easily 
formed in the cold. By assuming the first formula as 
correct, the constitution of amethenic acid would be— 
H 3 C\ 
h 3 c/ 
CH—CH.,—CH—CH—CH„OH. 
\/ 
O 
which represents an alcohol and not an acid. Accepting 
the second formula, we should have for amethenic 
acid— 
H 3 C/CH— c H 2 —CH 2 —CO. OH. 
which would be a strong acid, because it contains the 
group carboxyl, and, moreover, no acetic acid could be 
formed at the same time. 
It appears, therefore, most probable that one of the 
following formulae represents the constitution of diamy¬ 
lene. 
H 3 C 
CH, 
\/ 
CH 
H 3 C CH, 
\/ 
CH 
H 3 C ch 3 
\/ 
CH 
CH- 
CH,- 
A 
-CH 
I 
-CHo. 
CIL—CH 2 
I I 
CH—CH 2 
I 
CH 
/\ 
h 3 c ch 3 . 
The acid would then have one of the following for¬ 
mulae:— 
H a C ch 3 
\/ 
OH OH CH 
CH 3 . 
Besides the olefines which are derived from compounds 
having the general formula C n H 2n+1 R (R representing a 
monad radical), by the abstraction of HR, there exists 
another group, formed by the polymerization of the mem¬ 
bers of the first group. Of these poly-olenes, as Schneider 
calls them, only one, diamylene, has been more closely 
studied by this chemist (Ann. Chem. Pharm., clvii. 185). 
This. hydrocarbon, which is most readily formed by 
shaking amylene together with cold dilute sulphuric 
acid, yields, as the first product of oxidation, diamylene 
oxide, which by further oxidation splits up, with forma- 
n°TT °^. car ^ on dioxide, acetic acid, and amethenic acid, 
C;H 14 0 2 , a peculiar compound which is isomeric "with 
oenanthylic acid, from which however it differs by exhi- 
biting only very feeble acid properties. 
Erlenmeyer has shown that amylene has the following 
constitution:— 
h 3 c 
/CH—CH~CH,. 
H 3 C X 
Now as diamylene combines as easily with bromine as 
amylene does, it "would appear as most probable that in 
the former compound two carbon atoms are combined in 
the same manner as in other olefines, thus •— 
CH 2 
(!) i 3 3 c/CH-CH 3 -CHz;CH-CH 2 -CH 
CH 3 . 
ch 3 
I J 
(2) h 2 c=ch-ch—ch 2 -ch 2 -ch 2 -ch 
ch 3 
ch 3 . 
But if either of these two formulae expressed its con¬ 
stitution, two atoms of hydrogen would have to change 
places during its formation from amylene. This, how- 
CHo—O—CH CH—0—CH 
II I I 
CH-CH 2 CH 2 -CH,. 
h 3 c /N ch 3 . 
Both explain equally well why this singular compound 
HC=0 
is so weak an acid, as both contain the group 
CH 
or carboxyl in which half an oxygen atom is replaced by 
hydrogen. 
(To be continued.') 
THE LAST NEW METAL, INDIUM.* 
BY WILLIAM ODLING, ESQ., M.B., F.R.S. 
The word “ element ” is used by chemists in a peculiar 
and very limited sense. In calling certain bodies ele¬ 
ments, there is no intention on the part of chemists to 
assert the undecomposable nature or essence of the 
bodies so called. There is not even an intention on 
their part to assert that these bodies may not suffer de¬ 
composition in certain of the processes to "which they 
are occasionally subjected; but only to assert that they 
have not hitherto been proved to suffer decomposition; 
or, in other words, to assert that their observed beha¬ 
viour under all the different modes of treatment to which 
they have been exposed, is consistent with the hypothesis 
of their not having undergone decomposition. 
The entire matter of the earth then, so far as chemists 
are yet acquainted with it, is composed of some sixty- 
three different sorts of matter that are spoken of as 
elementary; not because they are conceived to be in 
their essence primitive or elementary, but because, 
neither in the course of nature nor in the processes of 
art, have they been observed to suffer decomposition. 
No one of them has ever been observed to suffer the loss 
* Lecture delivered at the Royal Institution, Jan. 19, 1872. 
