Grignard Eeagont on Cauiphorio aud Isocamphoric Esters. 7 



improvment in the melting point was observed. As the substance 

 was scanty, no furtlier study -of it was attempted. 



Tlie oxidation of diet]iylcam2)]iolicle : — Diethylcamphohde was 

 heated witli chromic acid mixture on a water-bath for five hours. 

 The oxidation went on with a brisk evolution of gases, and on 

 cooling, the oily substance solidified into fine needles. They were 

 then repeatedly recrystallised from dilute alcohol, and beautiful 

 lusti'ous feathery crystals, with a melting point of 60°, were 

 obtained. The substance is very easily soluble in alcohol, ether, 

 benzene, chloroform, carbon bisulphide, acetone, and petroleum 

 ether. It gave the following results on analysis: — 



0-1039 gave 0-2834 CO, and 0-0994 ILO. C=73-68 ; H= 10-60. 

 CisHonO-, requires C = 74-21 ; H=: 10-56 per cent. 



The molecular weight of the substance was determined by the 

 cryoscopic method, and a value well coinciding with the above 

 formula was obtained : — 



0-2532 in 17-56 benzene caused 0-335° depression. M=2l5-2. 

 Ci,H2,0, requires M = 210-2. 



on comparing this formula, C13H22O2, with that of the original 

 substance, C]4H2402, it may be seen that no increase in oxygen but 

 a diminution of CH2 took place by the oxidation. This means 

 that one of the three methyl groups in the camphor molecule had 

 been replaced by a hydrogen atom, and the following scheme of 

 the oxidation process seems to be most probale: — 



CH,-CH C(C.,H,5)., CH,-CH G(C.IIX CH.,-CH C(C.,H,)„ 



I I ' ' "I I ' ' 'I I ' ' 



C(CH3),0 C(CH3),Ü C(CHO.,0 



1 I -> I I -> I I 



CK,-C CO CH,-C CO CH.,-C CO 



I I "I 



CH3 CO,H H 



