

+ — 



+ +H 



C.H, 



:6:H Br 



and CH5 :6:H 





CMs 



C\H 



98 OXONIUM COMPOUNDS McINTOSH 



the starting point for a theory of complexes in solution. P'inally, 

 on electrolysis the organic molecule moves to the cathode, thus 

 showing direct combination between it and the hydrogen of 

 the acid. 



On the electron theory of valence these compounds, can 

 for the most part, be easily represented. For instance: C^H,« 

 O. HBr and C4HJ,, O. 2 HBr can be written: 



Br Br 



The hydrogen atoms share the electrons with the oxygen 

 and give to the group a single or a double charge; the electrons 

 from the hydrogen complete the bromine octets, which are, 

 consequently, negatively charged. The bromine ion and the 

 positively charged groups are held together by the electrostatic 

 force. These two compounds were isolated many years ago. 

 It is well, I think, to emphasize the similarity between 

 earlier formulae postulating quadrivalent or sexivalent oxygen 

 and newer views. These compounds were previously written: 



■LJ 



C2H5 „ H , C2H5 „ „ 

 LjHs Br L2H5 j^ ^ 



and in solution: 



+ + + 



C.H,_ -H - C.Hs H - - 

 C.H5 Br & O— Br Br 



C,Hs H 



In an analogous manner the graphica\ formulae of the alco- 

 hol, ketone, and ester complexes may be written without any 

 extension of the octet theory. Even the electrons in the rather 

 involved compounds (CHj COO CHj)! 5 H Br can be satis- 

 factorily grouped. The compounds-' mentioned by Lowry as 



4. Steele, Mcintosh and Archibald, Phil. Trans. (A) 205,99, (1905). 



5. Jour. Chem. Soc. Industry, 43.218. (1924). 



