ME. C. SCHOELEMMEE ON THE NOEMAL PAEAEEINS. 
117 
The iodide prepared from the alcohol boiling at 150° to 155° was subjected to frac- 
tional distillation; the largest portion of it boiled constantly at 170° to 171°. On 
decomposing it with potassium acetate, ^ was converted into hexene and f- into hexyl 
acetate, which boiled at 160° to 164°. The alcohol prepared from this acetate boiled 
now at 149° to 152°, and yielded on oxidation caproic acid, besides a not inconsiderable 
quantity of methyl-butyl ketone, from which it follows that it was still a mixture of 
primary and secondary hexyl alcohol. 
The difference between the boiling-points of the primary and secondary iodide is too 
small to effect in this way a separation of the alcohols. 
C H,) 
CO, was obtained, as well as caproic acid, by oxidizing the 
Methyl-butyl ketone , 
C 4 H 9 
mixture of the two hexyl alcohols, as described above. It is a colourless liquid with 
a pleasant smell, and boiling at 126° to 128°, which forms crystalline compounds 
with the bisulphites of the alkaline metals. It exhibits, therefore, all the properties 
of the acetone which Erlenmeyer and Waxklyn obtained by oxidizing methyl-butyl 
carbinol on the secondary hexyl alcohol obtained from mannite. On further oxidation 
it yields, like the latter compound, acetic and butyric acids, which were converted into 
the silver salts. 
Calculated for silver butyrate 
1st fraction, 
crystalline crusts, 
0-792 
2nd „ 
small needles, 
0-2758 
3rd 
small needles, 
0-3695 
4th 
shining, flat needles, 0-966 
Calculated for silver acetate 
55-38 per cent. 
gave 0-44 Ag= 55*56 per cent. 
„ 0T53 Ag=55-47 per cent. 
„ 0-2335 Ag=63T8 per cent. 
„ 0-646 Ag=64 - 85 per cent. 
64*67 per cent. 
In order to throw light on the constitution of hexane, it was necessary to investigate 
closely the butyric acid obtained from it. To isolate this acid, the aqueous distillates 
obtained in the oxidation of the acetone were repeatedly distilled, when the butyric acid 
came over with the first portions, whilst the greatest part of the acetic acid was left 
behind. The aqueous solution of the butyric acid thus obtained was neutralized with 
milk of lime and evaporated on the water-bath. The butyrate separated as a crystalline 
scum on the surface, which was not wetted by water. The cold saturated solution of 
this salt, contained in a sealed tube, was heated to 70°-80°, when shining laminae sepa- 
rated, which, on cooling, slowly but completely redissolved. This experiment was more 
than ten times repeated, always with the same results. The calcium salt possesses there- 
fore all the characteristic properties of normal calcium butyrate. 
The primary alcohol from hexane yielded as the product of its oxidation caproic acid, 
boiling at 200° to 205°. The silver salt is a white precipitate, which from a hot solution 
crystallizes in small needles. 
(1) 0*5029 of this salt gave 0-2444 Ag. 
