ACTION OF SODIUM 117 



in which lies a means of discriminating methyl alcohol, the 

 only one in which three hydrogen atoms are carried by 

 the carbon atom to which the hydroxyl is attached, primary, 

 secondary, and tertiary alcohols. 



(y) Examples from Inorganic Chemistry. The two 

 influences of hydrogen we have described are not confined 

 to organic chemistry ; a striking example may be found in 

 the inorganic region in the compounds of hydrogen with 

 nitrogen, ammonia, hydrazine, and Curtius' azoic acid 



NH 3 , N 2 H 4 , N 3 H. 



Both influences of hydrogen are to be seen, on the one 

 hand as increase of basic properties, shown by the two first 

 compounds in the form of hydrates, of which ammonia is 

 the stronger ; on the other, the decrease of acidity, since 

 azoic acid is converted by addition of hydrogen into the 

 base hydrazine. 



(6) Influence of the Light Metals, especially Sodium. 



(a) Examples from Organic Chemistry. The influence 

 of metals is like that of hydrogen, inasmuch as acidity 

 is diminished by introduction of a metal, apart from the 

 saturation which follows the replacement of the hydrogen 

 atom. In organic chemistry this is seen, e.g. in the malonic 

 esters : 



CO,C 2 H 5 CH 2 C0 2 C 2 H 5 , 



which form a metal derivative with sodium ethylate. 

 CO 2 C 2 H 5 CHNaC0 2 C 2 H 5 . 



The question why both the hydrogen atoms of the CH 2 

 group, since they are similarly placed, are not replaced by 

 sodium, giving 



C0 2 C 2 H 5 CNa 2 C0 2 C 2 H 5 , 



is answered by the fact that the acid character of the 

 compound is depressed by introduction of a metal, and 

 more by sodium than by the hydrogen which is simul- 

 taneously expelled. 



