298 PROCEEDINGS OF THE AMERICAN ACADEMY 



We are inclined to regard No. XII. with suspicion; but No. XIII. 

 alone shows that acetic ester has an even more unfavorable influence 

 than benzol on the formation of the sodic nitrite ; this is probably 

 due to the fact that in this case there is a tendency to form the tri- 

 bromdinitrophenetol, which would yield half as much sodic nitrite 

 as the tribrommononitroresorcine diethylether formed when benzol 

 was used. 



Relative Yields of the Organic Products. — After we had deter- 

 mined the amounts of sodic bromide and nitrite formed by the two 

 parallel reactions, 



C 6 Br 3 (N0 2 ) 3 + 3 NaOC 2 H 5 = C 6 (OC 2 H 5 ) 3 (N0 2 ) 3 + 3 NaBr, 

 C 6 Br 3 (N0 2 ) 3 + 2 NaOC 2 H 5 = C 6 Br 3 N0 2 (OC 2 H 5 ) 2 + 2 NaN0 3 , 



we tried to get an idea of the relative yields of the organic products. 

 This could be done with some approach to accuracy in the case of 

 the reaction which produces sodic bromide, because during tbe work 

 most of the trinitrophloroglucine trietbylether was converted into 

 the salts of trinitrophloroglucine or its diethylether, both of which 

 can be easily separated from the other organic products on account 

 of their solubility in water. With the tribromnitroresorcine di- 

 ethylether on the other hand, no such approach to accuracy was 

 obtained, because it could be purified only by crystallization, and 

 a large portion of it remained mixed with the viscous impurity 

 already mentioned. To obtain the following results, the organic 

 matter insoluble in water obtained from two experiments was re- 

 peatedly crystallized from alcohol, until as much pure tribromni- 

 troresorcine diethylether and trinitrophloroglucine triethyletber 

 had been obtained as possible. To the amount of the latter, which 

 was very small, were added tbe calculated amounts of the triethyl- 

 etber corresponding to the quantities found of free trinitrophloro- 

 glucine and its diethylether. Two pairs of experiments were 

 studied in this way, one from the series in which alcohol was the 

 only solvent, and one from that in which benzol was used. 



Experiments I. and II — Alcohol the only solvent. 20.71 gr. 

 of tribromtrinitrobenzol gave 12.75 gr. of organic matter insoluble 

 in water, from which were obtained 5.11 gr. of C 6 Br 3 NO 2 (0C 2 H 5 ) 2 , 

 1.4 gr. of the same slightly impure, 5.1 gr. of the semi-liquid frac- 

 tion from the mother liquor, and 0.49 gr. of C 6 (OC 2 H 5 ) 3 (N0 2 ) 3 . 

 From the aqueous solution 4.39 gr. of C 6 OH(OC 2 H 5 ) 2 (N0 2 ) 3 

 were obtained, corresponding to 4.77 gr. of the trietbylether, and 



