PROCEEDINGS OF THE AMERICAN ACADEMY. 



at 2<> was (i.7 172. Its molecular weight was ascertained by the freezing 

 point method : — 



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

 1.420. 



Calculated firi'-II,,. Pound. 



96 98 



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



The molecular refraction calculated from the density and molecular 



weight was : — 



Calculated for Found 



1 ! I ' 1 1 . C ); IIjrt CKg. 



30.06 31.77 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 chlorination takes doubtless de- 

 pends on the facl that the hydrogen in the side chain is Less firmly bound 

 than the hydrogen atom- in 'he methylene ring. The unsaturated con- 

 dition C 8 H 10 = CH 2 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 •_ , " I (»' D , formed by the 



action of sodium on methyl hexamethylene chloride, doubtless contains 



methylene rings: — ( '.-. II n ( 'I I ,. ( 'II ..(',-, II,,. The quantity of this 



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



-■in- for building up the higher methylene hydrocarbons containing 



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



shown by it- high specific gravity, 0.8872. 



1 inn .'i in I ill \ \mi i HI i.i m < Ihloridi . ' 1 1, -CI. 



The formula of dimethylhexamethylene was ascertained, as shown in 

 the pre\ion- paper, hy analysis and determination of its molecular weight 

 The formula was -till further verified by the formation of the chlorine 

 derivative. As in the chlorination of methyl hexamethylene, chlorine 



