50 
MR. C. SCHORLEMMER ON THE NORMAL PARAFFINS. 
a reversed Liebig’s condenser. As the hydrobromic acid which is evolved during the 
reaction carries off some of the volatile hydrocarbons, the upper end of the condenser 
was bent downwards and connected with a flask containing a solution of caustic 
potash, in which, however, the tube did not dip, as if that had been the case, the liquid 
would have been sucked back into the hydrocarbon when the reaction slackened ; one 
absorption flask was found sufficient to condense the hydrobromic acid completely. To 
ascertain, in the beginning of each experiment, whether all parts of the apparatus were 
tight, the cork of the flasks containing the soda solution was provided with a bent tube 
dipping into a little water. 
I. Normal Hexane. 
About 300 cub. centims. were heated in the large flask, and when briskly boiling, the 
stop-cock of the funnel-tube containing the bromine was so far turned that the liquid 
running down the tube was completely converted into vapour. On a bright day the 
colour of the bromine disappeared at once ; on a dull day, however, the action was 
much slower and ceased altogether in gas-light. It was very curious to observe how, 
on a clear day, when the sun was suddenly obscured by dark clouds, the flask became 
filled with brown vapours, which disappeared again as quickly as the clouds before the 
sun. 
The action was stopped before one-half of the hydrocarbon was attacked, and the 
product shaken with solid caustic potash, to free it from hydrobromic acid. On dis- 
tilling, the excess of hexane came over first ; the thermometer then began to rise, but 
even below 100° decomposition commenced, hydrobromic acid being evolved and a 
brominated liquid distilling over, while a black mass was left behind. In order to 
prevent this decomposition another portion was distilled with steam, but with no better 
success ; a tarry or carbonaceous matter was left behind, and the distillate contained 
besides hexane, brominated hexane, hexene, and hydrobromic acid. 
On submitting the brominated product to fractional distillation some of it began to 
decompose again, with the evolution of hydrobromic acid and blackening. But on 
continuing the distillations this decomposition gradually ceased, and a large quantity of a 
colourless liquid, boiling at 143 — 145°, and having a pungent and aromatic smell, could 
be isolated without difficulty. The low boiling point shows that this body was not 
primary hexyl bromide, which boils at 155 '5°. " Besides it, a small quantity of a higher 
boiling liquid was obtained, which, however, by further distillations yielded some more 
of the bromide boiling at 143 — 145°, while the highest boiling portion completely 
decomposed. The fractions distilling between 68° (the boiling point of hexane) and 
143° were very small, and consisted of mixtures of the hydrocarbon and the bromide, 
of which some more could be isolated by carrying on the distillation. 
The hexyl bromide was decomposed by heating it in sealed tubes with potassium 
* Lieben and Janecek, Liebig’s Ann., 187, p. 126. 
