MOLECULAR CONSTITUTION OF THE VOLATILE ORGANIC BASES. 
107 
the alcohol-radical ; but the question arose in what manner a portion of the base had 
been converted into hydrobromate ? It was not impossible that the bromide of ethyl, 
although it had been in contact with chloride of calcium, might nevertheless still 
have retained a portion of water, whose elements could have induced a regeneration 
of alcohol with simultaneous formation of hydrobromic acid : 
C 4 Hg Br-f 2 H 0=H O, C 4 Hg O-fH Br. 
V ^ ^ ^ 
Bromide of Ethyl. Alcohol. 
I now took care that both substances, the diethylaniline and the bromide of ethyl, 
should be perfectly dry before coming into contact. For this purpose, both liquids 
were left for several days over anhydrous caustic baryta and then subjected to distil- 
lation. The compounds at the common temperature were found to have no action upon 
one another. In order to place them in a condition most favourable for mutual action, 
the mixture was exposed for several days in a sealed tube to the temperature of boil- 
ing water. On opening the tube and extracting the mixture with water, a small quan- 
tity of hydrobromate was found to have nevertheless been formed. The portion 
insoluble in water was dissolved in hydrochloric acid and precipitated by bichloride 
of platinum. The salt obtained in this manner could not be mistaken. It fell down 
in the form of a yellow oil, which rapidly solidified into the orange-yellow crystal- 
line aggregates characterizing the diethylaniline-compound. 
From these experiments, it would appear that diethylaniline is no longer capable 
of fixing another equivalent of ethyl. Still the production of the small quantity of 
hydrobromate in the last experiment indicates that the phenomenon cannot be due 
to the formation of alcohol. Farther steps are necessary for the explanation of this 
transformation. 
In aniline, ethylaniline and diethylaniline, then we have three bases, which may 
be considered as derived from ammonia by the elimination and replacement of its 
three hydrogen-equivalents. The successive formations of ethylaniline and diethyl- 
aniline from aniline have been detailed in the preceding paragraphs ; the passage of 
ammonia into aniline, when exposed to the action of a phenyl-compound, has been 
proved at an earlier period by some experiments, made jointly by M. Laurent and 
myself, upon the action, at a high temperature, of hydrated oxide of phenyl on am- 
monia. In this reaction a small but unequivocal quantity of aniline is formed. 
The formation of aniline, ethylaniline and diethylaniline, appeared to have esta- 
blished in a sufficiently satisfactory manner, the point of theory which is here in 
question; still I thought desirable the acquisition of additional facts in support of 
the position to which this inquiry has conducted me. Thus I have been led to study 
the action of bromide of ethyl upon several of the derivatives of aniline, and to try 
whether other alcohol-radicals, such as methyl and amyl, would have a similar 
p 2 
