lOO 
It is also remarkable that in certain substances which possess the same 
odour, identical grouping in the molecule sometimes occurs, for example 
CHO 
O — 
O — 
in the vanillin and heliotropin groups, and the grouping 
CgHgCH = CH — 
in the cinnamic compounds. 
L. Balbiano and V. Paolinii) supplement their statements 2) with 
regard to the reaction of mercuric acetate on terpenes and compounds 
which carry a C3H5-group in the molecule. 
The ketone alcohol CiQHjg02 formed from 1-pinene is converted 
almost completely into carvacrol C^qH^^O by dilute sulphuric acid. 
From this follows, in agreement with the formation of terpenylic acid 
by oxidation, for the body Qo-^i6 02 constitution of a zl^-6-oxy- 
menthene-2-one : 
C .CH. 
(OH).C CH 
I II 
HC CH 
(OH) C 
CH. 
CCHg HOOC 
CO 
CO 
H 
C.CH(CH3), 
Carvacrol 
CH 
C CH(CHa 
3/2 
C(CH3), 
Terpenylic acid 
d-pinene yields with mercuric acetate the same oxidation-product, 
which proves that the oxidation simultaneously takes place in both 
asymmetric carbon atoms of the pinene-formula drawn up by Wagner 
and V. Baeyer. 
The mercury compound formed on treatment of camphene with 
mercuric acetate has been found to be a mercuric addition-product 
of the formula C^QH^g 0(Hg Cg H3 03)2, which, as we already mentioned 
in our April Report 1903, can be converted into camphene by hydrogen 
sulphide. The same conversion takes place on reduction with sodium 
amalgam, or with zinc and soda liquor. The formation of an addition- 
product therefore confirms Wagner's assumption that the camphene 
molecule contains an ethylene-linking. 
^) Berliner Berichte 36 (1903), 3575. 
2) Berliner Berichte 35 (1902), 2995. — Report April 1903, 83. 
