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XXI. 



ON THE EE ACTIVITY OF THE ALKYL IODIDES. 



By F. G. DONNAN, M.A., Ph.D. 



[Read, February 16 ; Received for Publication, February 19 ; 

 Published, March 30, 1904.] 



Where an alkyl iodide and silver nitrate react in the absence of a 

 dissociating solvent such as alcohol or water, the normal formation 

 of an ester occurs : i.e., 



EI + AgN0 3 = R • N0 3 + Agl. 



Thus, as is well known, this reaction can be carried out by allowing 

 solid silver nitrate to act on the alkyl iodide either alone or dis- 

 solved in dry ether. When, however, a dissociating solvent such 

 as alcohol is present, the main reaction may take quite another 

 course, the quantity of alkyl nitrate formed becoming in many 

 cases relatively unimportant. As shown by Nef, 1 there is usually 

 a large production of free nitric acid and an ether, some olefine 

 being also found in certain cases. These results are explained by 

 Nef by means of a dissociation-hypothesis, in which intermediate 

 dissociation-products of the alkyl iodide, containing either free 

 carbon valencies or divalent carbon, are supposed to be formed. 

 Nef 's hypothesis may be illustrated by a reference to the case of 

 ethyl iodide. The following reactions are supposed to occur : — 



/ 



1 Lieb. Ann., vol. 309, p. 126. 



