FUNDAMENTAL CONCEPTIONS 201 



of silver and mercury are reduced to metals with violence at 40, 

 alkylisocyanates being first formed. This shows the great affinity of 

 bivalent carbon for oxygen. 



(4) Primary amines and hydroxylamine, 



RN = C/+H-NHR 

 H 

 or H-NHOH-*RN = C^ 



NHR 

 H 



or RN=C/ 



NHOH 



giving amidines or oxyamidines. 



(5) Alcohols in the presence of an alkali are absorbed, giving 



H 



imido ethers, RN=C 



OR t 



(6) Hydrogen sulphide and mercaptans give readily at 100 the 



H 



H 



/ 



addition products RNH C=S and RN=C 



SR, 



(7) Adds. Aqueous mineral acids act with great violence on the 

 isonitriles giving primary amines and formic acid : 



H 

 RN=C/+2H 2 0->RNH 2 + ^C:O. 



In the absence of water and on diluting the alkylisocyahides with 

 absolute ether, perfectly dry halogen hydride causes the separation 

 of white hygroscopic salt-like substances of the empyrical formula 

 2RNC, 3HX[X=C1 Br or I]. For this reason Gautier as well as 

 Hofmann supposed the isonitriles to be basic compounds, i. e., sub- 

 stances behaving like ammonia hence the name carbylamine was 

 given them by Gautier. Further study has shown, however, that 

 this conclusion was erroneous. The isonitriles are entirely devoid of 

 basic properties; the great violence with which they act with halogen 

 hydrides is due to the presence of unsaturated carbon. The reaction 

 probably takes place as follows: 



