136  Volatile  Oil  from  Canada  Balsam.  [Amii£ciLw&tm' 
FRACTION  I. 
The  bottle  containing  this  fraction  was  filled  completely  and  well 
stoppered.  The  oil  possessed  a  pale  straw  color  and  a  terebinthi- 
nate  odor.  Its  relative  density  was  found  to  be  0-900  at  200  C.  In 
a  100  mm.  tube,  it  deviated  the  ray  of  polarized  light  24-83°  to  the 
left;  hence,  [a)  D  equals  —  27-59°. 
Since  Mr.  Kressin  had  not  determined  any  other  constant  than 
the  boiling  point  of  this  fraction,  no  comparisons  could  be  made.  Mr. 
Kressin's  note  (page  67)  refers  to  Fraction  II,  not  Fraction  I,  of  Mr. 
Kradwell.  However,  one  will  certainly  not  go  far  amiss  to  suppose- 
that  the  (a)  D  for  this  fraction  was  about  —  340  (compare  table 
P.  67). 
Upon  analysis  this  fraction  yielded  the  following  results: 
I.    0-2034  gms.  of  substance  yielded  0-1914  H,0  =  0-02125  H. 
and  0-6191  CO,  =  0-1688  C.  * 
II.    0-2182  gms.  of  substance  yielded  0*2324  H.O  =  0*0258  H. 
and  0-6638  CO,  =  0-18103  C. 
Calculated  for  C10H16.  Found. 
*~  I.  II. 
Per  Cent.  Per  Cent.      Per  Cent. 
C.    88-23  83-01  82-96 
H.    11*76  IO"45  11*83 
Although  the  boiling-point  of  this  fraction,  as  well  as  its  odor, 
indicated  the  presence  of  pinene,  the  amount  of  oxygen  present, 
6  5  per  cent.,  clearly  indicated  that  it  was  by  no  means  pure. 
That  pinene  is  present  in  the  oil  has  been  clearly  demonstrated. 
That  it  is  present  also  in  this  fraction  was  shown  by  means  of  its 
nitroso  chloride,  6  54,  10-17  and  11-25  per  cent.,  respectively,  being 
obtained  in  three  different  experiments.  That  the  yield  should  be 
much  greater  in  these  experiments  than  in  those  made  by  Mr. 
Kradwell  and  Mr.  Kressin,  is  now  easily  understood,  if  one  takes  into 
consideration  the  results  of  E.  W.  Smith  on  the  yield  of  nitroso 
chloride  of  pinene  from  oils  of  different  rotatory  power.1  The 
decrease  in  the  rotatory  power  of  this  fraction,  after  two  years,  stand- 
ing, is  sufficient  explanation  for  the  increased  yield  of  nitroso  chlo- 
ride. The  melting  point  of  the  nitroso  chloride,  after  purification, 
was  found  to  be  rather  high,  viz.:  107°  C.  However,  the  nitrol- 
benzyl-amine  base  closely  resembled  the  nitrol-benzyl-amine  pinene. 
It  melted  at  122°  C. 
Proc.  Wisconsin  Phar.  Assoc.,  1891. 
