MOLECULAR CONSTITUTION OF THE ORGANIC BASES. 
371 
It now remained only to submit the new base again to the action of iodide of ethyl. 
An experiment on a small scale showed that the two compounds do not fail to act 
promptly upon one another. The mixture, after an hour’s ebnllition in a sealed tube, 
solidified into a beautiful crystalline mass. In order to obtain a precise notion of this 
reaction, I repeated this experiment upon a grand scale. Two ounces of iodide of 
tetrethylainmonium were caustified by protoxide of silver, and then submitted to the 
action of about half a pound of iodide of ethyl. The mixture was kept boiling in a 
glass flask, provided with a long tube, in which the volatilized substances v»'ere con- 
densed and returned to the seat of the reaction. Daring the whole process not a trace 
of permanent gas was disengaged. After a day’s ebullition the solution had become 
neutral, and deposited on cooling magnificent crystals of iodide of tetrethylammonium, 
which were identified by analysis. In fact, for the determinations III. and V., men- 
tioned at the analysis of the platinum-compound, the salts had been prepared with 
the base obtained in this manner. On submitting the mother-liquor of the crystals 
to distillation in such a manner as to collect only the most volatile products, a con- 
siderable amount of perfectly pure alcohol was obtained, which was identified by a 
careful comparison of all its properties. The action of iodide of ethyl upon oxide 
of tetrethylammonium is therefore represented by the following equation — 
C4H51 
C4H5 
C4H5 
0 , HO-f C4 H5 I=C4 H5 0 , H 0 + < 
C4H5 
C4H5 
C4H5J 
LC4H5J 
I have since found that metallic oxides, such as protoxide of silver, in the presence 
of water, all exert the same action on iodide of ethyl ; in this case a metallic iodide is 
formed, alcohol being reproduced. 
The experiment just described shows that, as might have been expected, the 
ethylation cannot be carried on ad infinitum, and that the oxide of tetrethylammo- 
nium is the highest term attainable in the ethyl-series. The latter substance con- 
tinues to act upon iodide of ethyl, but the change affects solely the iodide of ethyl, 
while the base is no longer altered. 
The preceding researches are, in themselves, sufficient to establish the point of 
theory which is here in question ; still I hoped to gain a broader basis for raising 
general conclusions by collecting some additional facts. The repetition in the 
methyl- or amyl-series of an experiment already made in the ethyl-series, resembles, it 
is true, the working of a design in blue or green, which has been previously printed 
in red. Nevertheless, irrespectively of the farther elaboration of the theory of homo- 
logues, which is still wanted, such experiments lead frequently to new and unex- 
pected observations, which often amply repay the trouble and tediousness of such 
inquiries. I therefore made the experiments which yielded the following results ; — 
