MABERY. — COMPOSITION OF PETROLEUM. 289 



was allowed to act on the hydrocarbon over water in ordinary daylight 

 until it was nearly all converted into the chlorine derivative. After 

 washing and drying, the product was distilled under atmospheric pressure ; 

 after several distillations the monochloride collected in larger part ac 

 168°-170°. The specific gravity of this product at 20° was found to be 

 0.9358. A determination of chlorine gave the following result : — 



0.2034 grm. of the oil gave 0.1973 grm. AgCl. 



Calculated for CgHuCI. Found. 



CI 24.21 24.01 



The molecular weight of the chloride was determined by the freezing 

 point method. 



0.7293 grm. of the oil and 25. G6 grms. benzol gave a depression of 

 0°.982. 



Calculated for CgHiBCl. Found. 



146.5 142 



The index of refraction in sodium light at 20° was 1.455, and the mo- 

 lecular refraction : — 



Calculated for CgUisCl. Found. 



41.69 41.60 



That the chlorine enters a side chain in this reaction, as in the case of 

 methylhexamethylene, appears from the ready formation of the nitril by 

 heating the chloride with alcoholic potassic cyanide. On diluting the 

 solution the nitril separated as an oil, with the characteristic odor of the 

 nitrils. It was saponified by heating with aqueous potassic hydrate. On 

 acidifying the solution, a solid was precipitated, with an odor characteristic 

 of the alpha-toluic acids; but the quantity obtained was not sufficient for 

 identification. It was probably raeta-methyl, alpha-toluylic acid. 



Trimethylhexamethylene Chloride, C9H17CI. 



This chloride was also formed, washed, dried, and fractioned under 

 atmospheric pressure. It came together in larger quantity at 186°-188°; 

 its specific gravity at 20° was 0.9380. The percentage of chlorine was 

 determined. 



0.2300 grm. of the oil gave 0.2041 grm. AgCl. 



