on Valerianic Ether, 455 



for the most part correct as far as they went, were little appre- 

 ciated at the time ; and the subject was neglected until a few 

 years ago, when it was taken up by Geuther, Greiner, Brandcs, 

 Frankland, Duppa, and myself. 



One result has come out with the greatest clearness, and 

 about it there has been absolute accord among all of us from 

 the very first, viz. there is no elimination of the alcohol-radical. 

 Neither acetate nor formiate nor valerianate of ethyl yields ethyl 

 by the action of sodium upon it. Chloride, bromide, and iodide 

 of ethyl, on the other hand, yield the radical ethyl (or hydride 

 of ethyl and olefiant gas, which together represent ethyl) by 

 treatment with potassium and sodium. In view of this funda- 

 mental difference between these two classes of ethers, and bear- 

 ing in mind that in mineral chemistry no such distinction be- 

 tween the behaviour of the different classes of calts of a metal is 

 to be found, I proposed in 1864 to regard the ethers of the 

 fatty acids as salts in which not the alcohol-forming, but the 

 acid-forming radical played the part of the metal. Acetate of 

 ethyl I proposed to regard as ethylate of acetyl. This view, 

 which has as yet not found much favour with chemists, is, as 

 was shown in my former paper, in accordance with most of the 

 known chemical history ] of these ethers (as, for instance, with 

 the direction taken v by the action of ammonia on them), and is 

 in itself rational. A priori, we should be inclined to pronounce 

 it more comprehensible that C 2 H 3 O, an already oxidized^ sub- 

 stance, should cling with less pertinacity to oxygen than C 2 H 5 

 should do. In other words, we should expect acetic ether to 

 split up during reaction into acetyl and peroxide of ethyl rather 

 than into peroxide of acetyl and ethyl. 



The researches of the chemists just mentioned, although agree- 

 ing with mine as to non-evolution of ethyl, differ from mine in 

 many fundamental particulars. Their various papers, which 

 are scattered through the chemical journals of the last five years, 

 show that the action of the alkali-metals was regarded as being 

 of a most complex order. Referring to Frankland and Duppa's 

 memoir in the Philosophical Transactions, it will be seen that 

 they regard acetic ether as polymerizing itself in presence of 

 sodium, and then being attacked by sodium, and giving off 

 hydrogen and alcohol, one equivalent of hydrogen for every 

 equivalent of sodium that takes part in the reaction. And 

 at the same time that this is going on, Frankland and Duppa 

 consider that another portion of acetic ether deports itself 

 quite otherwise, not polymerizing itself, but suffering a direct 

 replacement of more or less of its hydrogen by the alkali-metal. 

 According to me, on the other hand, the reactions of sodium 

 on these ethers are always simple, at any rate in the first stage : — 



