1865.] of the Lactic Series. 81 



same time its radical functions, when he ascribed to the crystalline com- 

 pound obtained in the preparation of zincmethyl the formula 



In the same memoir he also represented this compound as the analogue of 

 mercuric methiodide, -rr f CH 3 



More recently Buttlerowf has prominently drawn attention to this beha- 

 viour of organo-zinc compounds, and has succeeded in obtaining zincmethylo- 

 methylate, 



7n" / ^^3 



IOCH 3 ' 



in a condition approaching to purity, by passing a stream of dry air through 

 a solution of zincmethyl in methyl iodide. M. Buttlerow's success in 

 obtaining this body and his failure in converting it into zincmethylate, are 

 both probably due to the comparative insolubility of zincmethylo-methy- 

 late in methyl iodide, owing to which the first product of oxidation was, to 

 a great extent, protected from the further action of oxygen. When, how- 

 ever, ether is used as the solvent of zincethyl, the oxidized product remains 

 in solution until the first stage is passed, after which zincethylate is gradu- 

 ally precipitated until the second stage is completed. Indeed, as has been 

 shown in the memoir above referred to (Phil. Trans. 1855, p. 268), the 

 oxidation, instead of stopping at the first stage, proceeds even somewhat 

 further than the second, and the product formed does not possess a com- 

 position in any degree approaching that which M. Buttlerow asserts it to 

 have. This is evident from the following numbers, and from the circum- 

 stance that it does not effervesce in the slightest degree when mixed with 

 water : 



Percentage composition ._ 



according to Buttlerow's Percentage composition 



r H 7n T according to mean of 



formula C ffif } analyses. 



C.... .......... 34-53 25-43 



H ............ 7'20 5-32 



Zn ............ 4676 42-04 



O ............ 11-51 27-21 



100-00 100-00 



The existence of monatomic organo-zinc radicals receives further support 

 from the following experimental determinations, which also show the 

 functions of such radicals in the formation of the ethers of the lactic series 

 from ethylic oxalate. 



When zincethyl is added to leucic ether previously cooled in a freezing 

 mixture, each drop of the zinc compound, as it comes into contact with 

 the ether, hisses like anhydrous phosphoric acid when dropped into water. 

 Torrents of hydride of ethyl are evolved, and the mixture finally solidifies 

 to a white tenacious mass, which fuses on the application of heat, and does 

 * Bulletin de la Soc. Chim. August 1864. 



