214 REPORT—1904. 
may be produced by removing the elements of water from the alcohol 
formulated below.! 
CMe,0H CMe, 
CH | | 
eH’ | CH; /CH. Px 
| CMa” | OM Pe CH, | CH, CH, 
Cre | CO | | | | 
*"\ OMe” = eee co. ©. AGH = geen 
gig Se ~ 
CHMe CMe 
Oimphor Intermediate alcohol Dihydroencaryone 
(inactive enolic form) 
+ t 
CH, :CMe CHMe, 
| 
CH C 
cH) SCH cu,’ oH 
| LN Aes | 
CH, C CH, co 
ors Ze 
CHMe CHMe 
Dihydrocarvone Carvenone 
VI. Chemical Properties of Dynamic Tsomerides. 
The addition to a mixture of isomerides in equilibrium of an agent 
which forms a stable compound with one isomeride brings about a 
complete conversion into that form. Thus although ammonium cyanate can 
be converted completely into urea by evaporating its aqueous solution, 
the reverse change is readily brought about by digesting urea with silver - 
nitrate. 
(NH,),COZAmCNO>AgCNO 
Again, nitrocamphor can be converted equally readily and completely 
into the bromo- derivative of the normal form or the potassium salt of the 
pseudo form. 
; CH.NO, ye C:NO,H 
GHC | LOHud | 
CO 
v Nitrocamphor \ 
CBr.NO, Soe : NO,K 
CHC | e 
CO CO 
Bromo-derivative Potassium salt. 
This formation of two types of derivatives is one of the most important 
indications of dynamic isomerism, and is frequently observed even when 
only one of the isomerides can be isolated. Thus camphor and other 
ketones, which certainly do not yield more than the merest trace of 
enol, are readily converted into enolic benzoates 2 when boiled with 
benzoyl chloride ; again, although the conversion of pseudo into normal 
* Armstrong and Lowry, Zrans. 1902, 81, 1469. * Lees, Trans. 1903, 838, 152, 
