CONSTITUTION OF GLYCOCOLI- AND ITS DERIVATIVES. 39 



ing- upon the analogy between glycocoll and its trimetliyl derivative, 

 they represent the one by the open, and the other by the closed, 

 formula. This inconsistency on their jnirt is. I think, to ])e attributed 

 partly, at any rate, to the erroneous manner in which the modes of 

 formation of glycfjcoU have been hitherto represented. 



Thus, the producti(jn of glycocoll by the action of ammonia 

 upon chloracetic acid is always regarded as if taking- place by the 

 direct re})lacement of chlorine by the amidogen group — 



H.>C-;C1 + HjXIL ll.,C-XH., 



I " """""' = I +liCl; 



OC-OH OC-Oli 



it, therefore, requires a fLU-ther strain of mind to re[)resent glvcocoll as 

 an internal ammonium salt, 



HoC-NH. H2C-NH3 



I -> I I 



OC-OH OC-0 , 



and it is this awkwardness, no doubt, which has had much to do in 

 making authors hesitate in adopting the closed formula. 



The above universally employed representation of the mode of 

 formation of glycocoll is, h(jwe\er. errone(jus, inasnuich as it does not 

 take into account the evident fact that ammonium chhjracefate must 

 first be produced. In (jrder to obtain glycocoll Ijy this method, an 

 excess of anunonia must be employed, whicli not only goes to neutral- 

 lise chloracetic acid but also to form an anunonium chloride, 



Roscoe and Schorlemuiei-, they only employ the open formula iu describing the modes of 

 formation of glycocoll. Mono- and dimethyl glycocoUs are represented by the open, and 

 trimethyl glycocoll by the closed, formula. Strecker and Wislicenus ('l'ext Book: English 

 Translation, 416 [1885]) are more decidedly inclined to this theory; but still they are not quite 

 consistent, iu one or two places using the open formula and in several others the closed double 

 formula. The only work I have seen where the internal ammonium theory is exclusively 

 adulated, though on an iasufScieut ground, is the article on Glycocoll, contributed by Hell to 

 the Xeues HamhàJrterhuch der Cheime, III, 446 [1878]. 



