288 . PROCEEDINGS OF THE AMERICAN ACADEMY. 



at 20° was 0.7472. Its molecular weight was ascertained by the freezing 

 point method : — 



0.7116 grm. of the oil and 25.19 grms. of benzol gave a depression of 

 1.420. 



Calculated for C,H],. Found. 



96 98 



The index of refraction with sodium light was found to be 1.416. 

 The molecular refraction calculated from the density and molecular 



Found. 



32.34 



These values indicate that the unsaturated hydrocarbon contains a 

 double bond between the side chain carbon and a carbon atom in the 

 ring, confirming the position of the chlorine atom in the side chain which 

 is indicated by the ease with which it is replaced in the reaction with 

 potassic cyanide. The form that the chloriuation takes doubtless de- 

 pends on the fact that the hydrogen in the side chain is less firmly bound 

 than the hydrogen atoms in the methylene ring. The unsaturated con- 

 dition C6Hiij=CH2 is shown by the action of halogens and haloid acids, 

 and confirmed by the molecular refraction, which corresponds to the sum 

 of the atomic refractions assuming the double bond. 



This constituent of California petroleum is therefore identical with 

 methyl hexamethylene, which maybe formed by the addition of hydrogen 

 to toluol. 



The hydrocarbon with a boiling point 220^-230°, formed by the 

 action of sodium on methyl hexamethylene chloride, doubtless contains 

 two metliylene rings : — CeHiiCrTo-CH.Ce-Hu. The quantity of this 

 product formed was too small for identification, but it evidently affords 

 a means for building up the higher methylene hydrocarbons containing 

 more than one methylene ring. That it was a condensed hydrocarbon 

 was shown by its high specific gravity, 0.8872. 



DiMETHYLHEXAMETHYLENE ChLORIDE, CsHijCl. 



The formula of dimethylhexamethylene was ascertained, as shown in 

 tlie previous paper, by analysis and determination of its molecular weight. 

 The formula was still further verified by the formation of the chlorine 

 derivative. As in the chloriuation of methylhexamethylene, chlorine 



