100 OXONIUM COMPOUNDS MclNTOSH 



We have shown'" that an ether-bromine mixture even 

 when made at a comparatively low temperature and with the 

 greatest' care always contains hydrobromic acid, and we as- 

 cribed the conduction to the acid. Plotnikof replied to this 

 with perhaps more heat than the question merited. However, 

 the analogous compound with chlorine shows no conduction", 

 and for this reason I look on Lewis' formula as incorrect, -v- 



Substances such as hydrogen flouride, the alcohols, water, 

 acetic acid, etc., which show association in the liquid or gaseous 

 state have, according to Lewis, a dl-valent hydrogen atom. 

 Water can be represented as: 



H 



:6:H:6: 



H H 



If we accept this view — and of its convenience there can 

 be no doubt — we may write for the ether-bromine _ and the 

 alchol-bromine compounds the formula: 



C.Hs :6: Br C.Hs :0: 



H-C-H: Br and H 



CH3 CHj :6: Br 



H: Br 

 and perhaps a better view of the substitution of bromine in 

 ether is indicated in this representation than in any other. 



Further the unstable compounds containing a halogen 

 or hydrobromic acid and toluene may be easily represented if 

 we admit the possibility of a halogen atom being shared, 

 but the pairing of the inactive hydrogen atom of a methyl 

 group seems too great an assumption to make. It must be 

 remembered that these very unstable addition compounds are 

 formed only in the neighborhood of — 90°C. Possibly the de- 

 termination of the moleculcr surface energy at low temperature 

 might decide this point. Such a formula has the merit 



10. Johnson and Mcintosh Jour. Am. Chem. Soc, 31,1138 (1909). 



11. Mennie and Mcintosh, Trans. Roy. Soc. (Canada), 16,303. (1922). 



