I20 
The phenyl urethane of the alcohol melts at 82°. When heated 
with dry oxalic acid, it yields an unsaturated hydrocarbon C9 H^^, and 
in agreement with the above constitutional formula it can be oxidised 
with chromic acid into a ketone whose boiling point lies at about 
184^ to 185°. The semicarbazone of the ketone melts at 196^ to 
197°; the oxime (melting point about 79^) is very readily converted 
into the isomeric piperidone. 
^rr C = NOH CO NH 
CH — CH< ^^CH — CH,— > >CH — CH<; >CH — CH3 
C Hg C Hg 
The oxidation of the ketone with potassium permanganate yielded 
two ketonic acids, which were separated by the semicarbazones. 
I. ketonic acid CgH^gOg from the semicarbazone of the melting point 
167° to 168°. On further oxidation it yields a-methyl glutaric acid 
(melting point 77°) and has therefore the following constitution: 
COOH 
CH3. \ 
0>CH — CO NCH — CH, 
cn/ \ / 
CH, CH, 
2. ketonic acid from the semicarbazone of the melting point 140°. 
By oxidation with sodium hypobromite it yields isopropylglutaric acid 
CgH^^O^y and with potassium permanganate isopropylsuccinic acid 
(melting point 1 17°). The following constitution therefore belongs to it: 
^„ /COOH 
\CH — CH< /CO — CH„ 
C H3/ \ / 
and to dihydrocamphorone : 
CHg CH^ 
CH3 CO-. 
>CH — CH< >CH — CH3 
Q^/ \ / 
C Hg C 
c) Pinophorone. Pinophorone was obtained by Semmler in 
addition to acetone and an unsaturated hydrocarbon Cg H^^, by distillation 
of calcium pinonate. It boils at 203° to 205°, has the specific gravity 
0,9284, and the refractive index 1,4805. The semicarbazone melts 
at 157° to 158°. When it is decomposed, hydrocarbon is partly formed. 
The oxime, like that of camphorphorone, is converted instantly with 
mineral acids into piperidone C9H15NO, which can be split up into 
an amido acid CgHiyNOg. It follows from these reactions that the 
carbonyl-group of the ketone is situated in the nucleus. Pinophorone 
is unsaturated. The double-linkino^ remains in existence, even when 
