C479 ) 
Looking at the great value of the product in 5, it is to be expected 
that the acid 1:3:5 will be the chief product, while the others 
will only be obtained in minute quantity. In fact the 1. 3. 5. acid 
is the only dinitro-acid as yet obtained. 
In the nitration of p-nitrobenzoic acid the said products are : 
CO, H 
DEEN, 
p= ht HüÜBNeR and STROMEYER first obtained the 
6 21730 1. 2. 4 acid by this process and later on 
| Craus and HALBERSTADT working on a larger 
: 3\so, quantity of material isolated the 1, 3, 4 acid 
DN | which is no doubt formed to a smaller extent. 
NA 
N O, 
In the nitration of chloro-benzene at 0° a semi-solid crystalline 
mass is obtained; if care is taken to collect together all the products 
formed in the reaction this mass after being fused solidifies at 58°.9. 
It is known that ortho- and para-chloro-nitrobenzene are formed in this 
nitration; whether the meta compound is also formed in small quan- 
tities remains to be seen; at all events its presence in the nitrated 
mass is not stated in the literature. Since p- chloronitrobenzene melts 
at 82° and the ortho compound at 32°, it is evident from the soli- 
difying point that the para compound strongly predominates, so that 
the relation will be: ortho little, meta traces, para very much. This, 
and the relation in which the three nitrobenzoic acids are formed, 
proves that in the nitration of ortho-chloro-benzoic acid, the acid 1: 2:5 
(CO, H = 1) ought to be formed in large predominating quantity toge- 
ther with small quantities of the acid 1:2:3; in the nitration of 
m-chlorobenzoic acid the acid 1:3:6 should be chiefly formed, 
the acid 1:3:2 occurring only in small and the other isomers in 
very trifling quantities; in the nitration of p- chlorobenzoic acid the 
acid 1:4:3 should be almost exclusively formed. This quite confirms 
the recent research of MONTAGNE ?). 
In the literature, nothing much is said about the relative quan- 
tities of the isomers formed in the nitration of benzene derivatives ; 
as a rule the writers confine themselves to such statements as “chief 
product”, or ,much’’ of this „little” of the other isomer. With the 
aid of such statements it is possible to ascertain whether the above 
rule is of general application. This seems indeed to be the case. 
!) Dissertation, Leiden 1899. 
