OXOXIUM COMPOUNDS MCINTOSH 101 



that it indicates the easy substitution of chlorine or 

 bromine; benezene gives no compounds with hydrobromic 

 acid." 



Experimental 



A few typical compounds have been made and analysed 

 with the object of testing somewhat further the rules given for 

 the combination of the halogens and organic substances. These 

 complexes do not differ from those previously made. They 

 melt at low temperatures, are formed with a slight heat evolu- 

 tion, and when substitution is prevented do not conduct. The 

 methods employed have been given in previous papers. 



Normal propyl alcohol. This hydroxide gives compounds 

 with both the halogens. With bromine the solution is so viscid 

 that it is impossible to trace the freezing point curve or to 

 obtain the compound pure enough for even an approximate 

 analysis. Chlorine gives a white, crystalline compound, 

 melting below — 80°C. The analysis show 35.3, 38.1 per cent, 

 chlorine; propyl alcohol with one atom of chlorine contains 

 37.2 per cent. No compound could be made with iso-propyl 

 alcohol. 



Normal and isobutyl alcohols. No compounds were ob- 

 tained, due perhaps, to the syrupy solutions. The halogens 

 appear to act more quickly on the iso-alcohols at low tempera- 

 tures than on the normals. 



Methyl ethyl ketone. The chlorine compound contained 

 43.6, 45.9 per cent, halogen. Required for two halogen atoms, 

 49.7 per cent. The bromine complex melted at — 32°. Found 65.4, 

 64.4 bromine. For two brortiine atoms 69.0 percent, is necessary. 



Methyl acetate. The chlorine compound melts at — 70". 

 It contained 58.0, 57.4 per cent, chlorine. CHj COOCHj 3C1 



Note. — I have said nothing of a new view — the group molecule. This 

 conception seems to be of doubtful value as far as the oxonium compounds 

 are concerned, but convenient and useful. in a discussion of the combinations 

 of the hydrocarbons. 



12. Maass and Russel. loc. cit. 



