NEF. — BIVALENT CARBON. 169 



It follows from the above that on treating silver fulminate with 

 dilute hydrochloric acid (one molecule) an addition of hydrogen chlo- 

 ride to the unsaturated carbon atom in this salt takes place, 



AgON : C + HCl = AgON : C^j • 



The addition product, which is soluble in water, is then, in the second 

 stage of the reaction, further acted upon by some of the hydrogen 

 chloride present, aild converted partially into silver chloride and for- 

 mylchloridoxime, 



AgON : C^j + HCl = HON : C^j + AgCl. 



This experiment demonstrates, therefore, in a very pretty manner, 

 that an organic silver salt can react with hydrogen chloride, leaving 

 the silver present in the molecule entirely intact. The bivalent carbon 

 atom present in fulminate of silver is so reactive, that the metal is 

 not affected at all. I have already repeatedly, in other cases, drawn 

 attention to similar reactions ; the double bond present in sodium 



acetacetic ether, 



CHg - CONa 

 II 

 HCCO.R, 



is so reactive that, on treatment of this salt with alkyliodides and acid 

 chlorides,* exclusively or chiefly an addition of these reagents to the 

 double bond takes place, and the sodium atom remains entirely intact 

 in the whole reaction. The same phenomenon has also already been 

 proved to take place with many other silver salts, t 

 The isolation of the intermediate product, 



C:NOAg, 



in the above instance therefore furnishes a further very important 

 experimental confirmation of the processes which I have shown 

 take place in the interaction of acetacetic salts with alkyliodides and 

 acid chlorides. A further entirely analogous example of addition is 

 furnished by the study of the action of hydrogen sulphide on silver 

 fulminate. On adding to silver fulminate, suspended in water con- 



* Ann. Chem. (Liebig), CCLXVI. 52, CCLXX. 331, CCLXXVI. 200. 

 t Ann. Chem. (Liebig), CCLXX. 329, CCLXXVI. 234, CCLXXVII. 73 

 Of. also page 147 of tlie preceding paper. 



