340 Wisconsin Academy of Sciences , Arts and Letters. 
Bouchardat and Lafont 11 report (1886) on a series of experiments per¬ 
taining to the action of acids on the terpenes. The action of acetic 
acid on pinene furnishes a mixture of acetates which can be separated 
by means of fractional distillation under diminished pressure. The 
separated acetates yield upon treatment with alcoholic potassa optically 
active terpineol and borneol respectively. Whereas, by this treatment 
pinene could be converted into terpineol and borneol, camphene could 
be converted into borneol only, dipentene into optically inactive ter¬ 
pineol, dextrogyrate limonene 12 into dextrogyrate terpineol. From the 
o-terpineol they obtained crystals at a very low temperature. 
With the introduction of new terms, viz.: “ terpilenol ” and “ terpol ” 
for terpineol, and of “terpal” for cineol Bouchardat and Voiry 9 (1887) 
have rendered poor service to science. Their disregard of the results 
achieved by others certainly is not honorable. 
( 1879 ) 
Flawitzky 7 j ^gg^ j prepared optically active monohydrates, which he 
termed “ Terpenhydrate,” by treating dextro — and laevogyrate pinene- 
with alcoholic sulphuric acid. No doubt, these terpenehydrates as well 
as'the “ terpilenoles ” of Bouchardat are optically active terpineols inacti¬ 
vated more or less by the presence of optically inactive terpineol. 
When dehydrated with acetic acid anhydride they yielded optically ac¬ 
tive hydrocarbons C 10 H 16 which Flawitzky termed “ Isoterpene ” and 
which, to judge by their properties were more or less impure limonenes. 
Properties. 
Terpineol is a viscid 13 liquid 18 of agreable odor, 14 lighter than and in¬ 
soluble in water, readily soluble in alcohol. It is volatile with water 
vapors and boils between 215-218° 15 . That obtained from dipentene and 
and terpin is optically inactive, 6 that obtained from optically active 
pinene and limonene is optically active. 17 
Terpineol is an unsaturatod compound. 19 The addition of water con¬ 
verts it into terpin and its hydrate. 20 The removal of a molecule of water 
dehyrates it according to reagents and conditions to dipentene, 21 ter- 
pinene or terpinolene, 22 but never to pinene. The hydrohalologen acids 
convert terpineol like terpin into the dihydrohalogen addition products 
of dipentene i. e. the dihalogen esters of the diatomic alcohol but not 
into a monohalogen ester of the monatomic alcohol terpineol 23 , probably 
according to the equation. 24 
C 10 H 17 OH + H Cl = C 10 H 1S | 3^ 
Cio H 18 | oh + H Cl = C 10 H- 18 Cl 2 + H 3 O. 
The monohydrochlorides of the limonenes, no doubt are to be regarded 
as monochlorine esters of the terpineols. 25 Apparently the acetic ester 
can be prepared from the alcohol. 26 When saponinfied with alcoholic 
