272 PROCEEDINGS OP THE AMERICAN ACADEMY 



The broradiuitrophenylacetacetic ester is saponified and decomposed 

 by heating with sulphuric acid of specific gravity 1.44, giving the 

 bromdinitrobenzylmethylketone, 



C 6 H 2 Br(N0 2 ) 2 CH 2 COCH 3 , 



but no trace of the corresponding acetic acid. This ketone melts at 

 112°— 1 13°, and also possesses acid properties, giving a purplish red 

 salt soluble in alcohol, but decomposed almost completely by water. 

 The acid properties of the ketone are less marked than those of the 

 acetacetic ester, as was to be expected, since the hydrogen, which is 

 replaced by basic radicals, is subject to the influence of an acetyl, a 

 carboxylester, and a dinitro phenyl group in the acetacetic compound, 

 only to those of an acetyl and a dinitro phenyl group in the ketone. 



The bromine of the ketone can be replaced easily by the aniline 

 radical C 6 H.NH, forming anilidodinitrobenzylmethylketone, 



C 6 H 2 (C 6 H 5 NH)(N0 2 ) 2 CH 2 COCH 8 , 



which melts at 131°, and has not lost all acid properties, although 

 they have been much weakened by replacing the bromine atom by the 

 basic radical C C H.NH. It cannot form an ammonium salt, but the 

 sodium salt can be easily obtained in alcoholic solution, and on analysis 

 gave a number corresponding to the formula 



CJI J (C ti H 5 NH)(NO,),CHNaCOCH 3 . 



It is completely decomposed by water, but dissolves in alcohol with a 

 brown color. 



Both these ketones, therefore, show stronger acid properties than 

 desoxybenzoine C 6 H.COCH 2 C 6 H 5 , the metallic compounds of which, 

 according to Victor Meyer,* could not be isolated ; we are inclined to 

 ascribe this to the presence of the nitro groups in the phenyl, which 

 would heighten its acid-producing power, but it may also be due in part 

 to the fact that those ketones contain the acetyl group, which, as 

 Claisen and Ehrhardtf have pointed out, has a greater influence in 

 producing acidity than the benzoyl radical contained in desoxy- 

 benzoine. 



The hydrazone of the anilirlodinitrobenzylmethylketone, 



C 6 II. 2 (C 6 tI 5 NII)(N0 2 ) 2 CII 2 C(NNHC 6 H 5 )CH 3 , 



was also prepared, and melted at 140°. 



The full details of the work will be found in the remainder of the 

 paper. 



* Ber. d. ch. G. 1888, p. 1291. t Ber. d. ch. G. 1889, p. 1019. 



