92 Action of Sodium and Iodide of Ethyl on Acetic Ether. [Recess, 



which theory is emhodied in four equations expressive of Frankland and 

 Duppa's view of the origin of the wax-like mass . As I have already pointed 

 out, each one of these four equations affirms the evolution of an equi- 

 valent of hydrogen by every equivalent of sodium employed. 



I have shown that acetic ether does not evolve hydrogen by reaction 

 with the alkali metals. Equations which assume evolution of hydrogen 

 in these reactions are therefore, in my opinion, inadmissible. 



At the end of my paper in the January Number of Liebig's ' Annalen,' 

 I promised to give an explanation of Frankland and Duppa's products, 

 which should not involve the assumption of evolution of hydrogen. That 

 explanation I now give. 



On reference to Frankland and Duppa's paper just cited, it will be found 

 that the products described by them as obtained from the " wax-like 

 mass " and iodide of ethyl are the following : — 



A. C a H 14 0 3 , liquid boiling at 195° C, 



B. C 10 H 18 0 3 , liquid boiling at 210° C. to 212° C, 



butyric ether, caproic ether, and also some unacted upon acetic ether, and 

 a considerable quantity of common ethylic ether. 



The history of these compounds is therefore the task set before me. 

 I have already shown that the direct products of the action of sodium on 

 acetic ether are ethylate of sodium and sodium-triacetyl. Nothing else 

 seems to be produced directly. But the excess of acetic ether, which is 

 necessarily taken, acts on some of the ethylate of sodium, producing alcohol 

 and acetate of ethylene-sodium in the manner described by me on a 

 former occasion. (Of course the extent to which this secondary action 

 takes place will be determined by the exact circumstances of the experi- 

 ment.) We have, therefore, in the wax-like mass got by prolonging the 



action of sodium on acetic ether : — 



Ethylate of sodium C 2 H. NaO 



Sodium-triacetyl C G H 9 Na 



Acetate of ethylene-sodium C t H. Na 0 2 



Alcohol C 2 H^O. 



On the first three iodide of ethyl acts, giving iodide of sodium and 

 organic liquids. 



From the ethylate of sodium comes the common ether. 



From the sodium-triacetyl comes ethyl-triacetyl, which is A = C 8 H u 0 3 , 

 having been got by Geuther from the pure sodium-triacetyl. 



From isolated acetate of ethylene-sodium and iodide of ethylene I have 

 recently obtained liquid B, C 10 H 18 0 3 , thus : — 



Acetate of ethylene- 

 sodium. Alcohol. 



2C 4 H 7 Na0 2 + 2C 2 H s I = 2Na I + C 2 H e O + C 10 H 18 0 3 . 

 The liquid prepared by me boiled at 212° C, and gave carbonate of 



