Mr Jones, The Solubility of Stereoisomerides, etc. 
27 
Tice Solubility of Stereoisomerides in Optically Active Solvents. 
By H. 0. Jones, M.A., Clare College. 
\Read 26 November, 1906.] 
Some text-books of Organic Chemistry make the statement 
that 'the solubilities of two optical antimers must be different 
in an optically active solvent’; this statement is not supported 
by any experimental evidence. 
If this statement were true crystallization of a d + 1 mixture 
from an active solvent should be a simple and elegant method of 
separating such a mixture into its components. Further, it would 
have an interesting bearing on the theory of solutions since it is 
difficult to see how there could be a difference in the solubility 
for d and l compounds unless there was combination between 
solvent and solute. 
The subject was, therefore, considered to be worth investi- 
gating experimentally. 
The solubility of d and l camphor and of d and l camphoroximes 
in purified turpentine (cl pinene) and in pure l amyl bromide was 
therefore examined. 
The following data show that the compounds used were pure : 
d camphor [a] B in 8 per cent, solution in ethyl alcohol at 18° C. + 41-9°, 
l „ [a] D „ „ „ „ „ ~41-8°, 
d camphoroxime [a] 0 in 3 per cent. ,, ,, „ ,, - 400°, 
l „ [a]j, „ „ „ „ „ + 39 - 9°. 
The l amyl bromide gave 
a n = + 4‘6° in a 1 decimetre tube at 18 C. 
The turpentine used gave 
cl d — 4 - 38° in a 1 decimetre tube at 18° C. 
It was found that the camphorsulphonic acids were not 
sufficiently soluble to make determinations of solubility possible 
and that the two borneols could not be obtained pure enough for 
the purpose. 
The solvent and solute were allowed to stand together and 
shaken from time to time at a constant temperature until the 
rotatory power of the solution became constant. The specific 
gravities of the solutions of the d and l compounds were then de- 
termined and, in the case of the camphoroximes in turpentine, 
the solubility was determined directly by evaporating a weighed 
