SUBSTITUTION OF CHLORINE FOR HYDROGEN. 7*7 



volume. M. Dumas afterwards repeated the experiment with 

 oil of turpentine, and obtained a similar result ; 4H in the latter 

 body being replaced by 4C1, or C 20 H 16 becoming C 20 H 12 C1 4 . 

 The action of chlorine on a great number of organic substances 

 has since been observed by MM. Dumas, Laurent, Regnault, 

 Malaguti and others, and found to be remarkably uniform. The 

 investigation has led to the formation of a large number of new 

 compounds, and to the propagation of certain theoretical views 

 by M. Dumas, which have had an extraordinary influence on 

 the recent progress of organic chemistry. 



When light carburetted hydrogen gas C 2 H 4 , is allowed to mix 

 gradually with three times its volume of chlorine, in strong 

 sunshine, the whole 4 eq. of hydrogen are converted into hydro- 

 chloric acid, which is liberated, while the 2 eq. of carbon com- 

 bine with 4 eq. of chlorine, and form a peculiar liquid chloride 

 of carbon C 2 C1 4 ; so that the hydrogen of the former compound 

 appears to be simply replaced by chlorine in the latter.* The 

 removal of the whole hydrogen by chlorine takes place at once, 

 in this hydrocarburet without the formation of any other inter- 

 mediate product except a trace of chloroform, but in other cases, 

 where there are several equivalents of hydrogen, the latter are 

 often removed and replaced by chlorine one by one, and a series 

 of bodies formed in which while the hydrogen diminishes, 

 the chlorine increases in an equal proportion; such are the 

 compounds produced by the action of chlorine on Dutch liquid 

 already described (page 375), and the remarkable series produced 

 by the repeated action of chlorine upon hydrochloric ether.f 

 The two series referred to, exhibit a remarkable isomerism, the 

 corresponding products having the same composition although 

 distinguishable by their physical properties and by the effect of 

 re-agents upon them. These chlorine compounds are all vola- 

 tile liquids, with the exception of the solid perchloride of carbon, 

 which is common to both series. 



* Dumas, An. de Ch. et de Ph. t. 73, p. 94. 

 f Regnault, An. de Ch. et de Ph. t. 71, p. 353. 



