Action ofPentachloride of Phosphorus onHydride of Bcnsoyle. 365 



acid ; and this with iodide of methyle are the only products of 

 the action. The iodide of methyle treated with oxalate of silver 

 yielded oxalate of methyle, from which pure methylic alcohol 

 was prepared. The best means of producing the above decom- 

 position is to heat acetone with concentrated aqueous hydriodic 

 acid in closed vessels. 



If, according to the above view, the acetones are aldehydes 

 in which hydrogen is replaced by an alcohol radical, we might 

 expect to obtain the acetones by the action of the iodide of an 

 alcohol radical on the metallic compounds of the aldehydes. 

 Ebersbach* has tried this experiment with valerianic aldehyde, 

 expecting the action to be in accordance with the equation — 



CIO H9 on ^ p, TT5 T c^o H9 on ^ ^ ^ 



Na |+C^Hn= ^,j^5 l+Nal. 

 Sodium- valeraldehyde. Acetone. 



The sodium compound of valeraldehyde was obtained by add- 

 ing sodium to valeraldehyde, in which it dissolved with evolu- 

 tion of hydrogen and disengagement of heat, to a gelatinous 

 yellowish mass. Iodide of sethyle did not act on this in the cold, 

 and only slightly at 100° C. ; but heated to 120° C. for some 

 time, a large quantity of iodide of sodium separated. The mass 

 was then washed with water, the excess of iodide of sethyle re- 

 moved by heating in the water-bath, and the liquid then frac- 

 tionally distilled. In this way a product boiling at 200° C. was 

 obtained, heavier than water, and not miscible with it, readily 

 soluble in tether and alcohol, with a pleasant a;therial odour and 

 a bitter taste. It yielded on analysis numbers agreeing with 

 the formula C'^ H'^ 0^. Hence it was not the compound 



Q4 jjo r, but was valeraldehyde in which two equivalents 



of hydrogen had been replaced by two equivalents of sethyle, 

 according to the equation 



CIO ip 0-2-1 c'OH^ on -f2NaL 



Na2 J-+-^ ^^ ^- {Qni^f J 

 Sodlum-valeraldehyde. New substance. 



By the action of pentachloride of phosphorus on hydride of 

 bcnzoyle, C'^ II'' 0'^, Cahours obtained chlorobeuzolc, C'"* 11^ CP, 

 and he regarded it as hydi'ide of benzoylc in which oxygen is 

 replaced by chlorine. Later investigations of Wickef and of 

 Engelhardt J seem to px'ovc that this is not the constitution of 

 the body, but that it is rather the chloride of a biatomic radical, 

 C* II*', analogous to olctiant gas. 



* Liebig's Annulen, June 18.58. 



t riiil. Mug. October lb57. J Chemical Gazette, vol. xv. p. 421. 



