( 421 ) 
Iii this investigation the reaction appeared to pass through the 
following phases: 
I (CH s ) 8 C.COC1 + H 2 S0 4 = (CHj), C.C0S0 4 H + HCI 
ir (CH S ) S ccoso 4 h = H 2 S0 4 -f CO + c 4 h 8 
in which the isobutene was again first polymerised and then dissolved 
on prolonged action of the acid, with formation of sulphonic acids 
(Bistrycki and Mauron Berichte 40 p. 4377) and sulphur dioxide. 
The chlorine atom is, therefore, first detached by the H 2 S0 4 and 
in an analogous manner we may expect the same from A1C1 S . 
Sulphuric acid itself supplies an H-atom; on using A1C1 S this 
hydrogen must be withdrawn from the acid-chloride so that the 
two phases noticed separately when sulphuric acid was employed as 
catalyst, coincide in this case. 
[It may be pointed out here that a 20°/ 0 “Oleum” acts almost as 
energetically as A1C1 3 . It is very probable that the real catalyst in 
sulphuric acid is the S0„ which in concentrated acid is not utterly 
paralysed by the H s 0 present]. 
Although the expulsion of the chlorine could be shown in a single 
(see above) instance only, I think I have succeeded in demonstrating 
from the progressive change of the reactions and also by indirect 
means, that the chlorine atom is rendered more movable. 
In the reaction of Friedel and Crafts we must imagine that 
besides the chloride, the benzene derivative, being an unsaturated 
compound, is also rendered active by aluminium chloride which 
undoubtedly will take place most readily when the chloride, catalyst 
and benzene derivative form one homogeneous phase. The significance 
°f the so-called ferments of G. Gustavson (J. pr. Chem. [2] 68 p. 
209—234) must be particularly looked for in the fact that these 
are very loose compounds in which the three kinds of molecules 
mentioned have arrived in each others, immediate proximity. 
The fact that the rays of light introduce the halogens into the 
elmin must, therefore, be explained by assuming that the double 
bonds of benzene are rendered less active by the chemical rays than 
the hydrogen atoms in the chain, whereas on the ^ other hand the 
latter are hot rendered quite so active by aluminium chloride. 
The experimental details of this research will be published elsewhere. 
Delft. Org. Chem. Lab. Techn. University. 
