26 



Frankland and Duppa — On the Acids [Mar. 1, 



and which exists not only in all acids of the lactic series, but also in nearly 

 every known organic acid. The isolated molecule of this radical is oxalic 

 acid, 



r C Ho 

 t C O Ho, 



in proof of which they show that when oxahc ether is acted upon by 

 nascent amyl, it is converted into caproic ether ; 



JCOEto , rCBuH,_^ rCBuH^ 

 \COEto"^ tCBuH,"^ jCOEto. 

 Oxalic ether. Amyl. Caproic ether. 



Oxalyl is closely related to cyanogen, the two radicals passing into each 

 other in a host of reactions ; hence the production of cyanides from the 

 ammonium- salts of the fatty acids on the one hand, and the synthesis of 

 acids from certain cyanogen compounds on the other, — a reaction first 

 pointed out by Kolbe and Frankland*, and which has of late yielded such 

 important results in the hands of Maxwell Simpson f and of Kolbe and 

 of Hugo MtillerJ. 



rcN'" rcoHo 



1 C N'" t C O Ho. 



Cyanogen. Oxalyl. 

 The researches of these chemists prove that the introduction of cyanogen 

 into an organic compound, and its subsequent transformation into oxalyl, 

 converts that compound into an acid, or, if already an acid, increases its 

 basicity by unity (for each atom of oxalyl so developed), this result being 

 apparently quite independent of the position of the oxalyl in the molecule. 

 The atom of oxalyl (as the above molecular formula shows) may be regarded 

 as methyl (C Hg), in which two atoms of hydrogen have been replaced by 

 one of oxygen, and the third by hydroxjd (Ho). 



It may be objected that the group of elements, which is thus invested 

 with radical functions, lacks one of the fundamental characteristics of a 

 radical by its proneness to change ; but this characteristic is exhibited by 

 the commonly received radicals in a very varied degree. And even methyl 

 itself, which certainly possesses it in the most marked manner, readily 

 permits of its hydrogen being replaced by chlorine or bromine on the one 

 hand, and by sodium on the other. All compound radicals, the authors 

 remark, are purely conventional groupings of elements intended to simplify 

 the expression of chemical change ; and in this respect they believe the 

 group oxalyl, entering as it does into the constitution of nearly every 

 organic acid, has as valid a claim to a distinct name as the most universally 

 recognized radical. Its admission renders possible the following very 

 simple expression of the law governing the basicity of nearly all organic 

 acids — an organic acid containing n atoms of oxalyl is n basic. 



The authors classify all acids of the lactic series at present known, or 



* Memoirs of Chem. Soc. vol. iii. (1847) p. 386. 



t Phil. Trans. 1861, p. 61 ; and Journ. Chem. Soc. vol. xviii. 



X Journ. Chem. Soc. vol. xvii. p. 109. 



