( 25V ) 

 Chemistry. "The nitration of p-chlorotolueney By Prof. A. F. 



Hoi. I, K.MAN. • 



The p-ch'lorotoluene required for this purpose was prepared by 

 Mr. van den Arend from pure p-toluidine b. p. 160 — 161° at 754 mm.; 

 in. |>. -\- 7°. Of both nitro-2?-chlorotoluenes the isomer 



CH„C1, NO, = 1,4, 2 

 was obtained by him from p-chlorotoluene by nitration and separation 

 of the mononitrocompounds ; it melted at + 38°. He prepared the 

 other isomer CH 8 , Cl,N0 a = l,4, 3 according to Gattermann's method 

 B. 18,1483 which may be expressed by the following scheme: 

 CH S CH, CH, CH, 



V \/NO, \/NO, X/NO, 



NHac NHac NH, CI 



The product obtained had a boiling point of 259 — 260 3 at759mm. 

 and melted at -}- 7 U in a capillary tube. The solidifying point was 

 -f 5°8. 



For the determination of the relative quantities of both isomers 

 present in the nitration product of p-chlorotoluene the solidifying 

 point determination process was again found to be the most suitable. 

 Hence the solidifying point curve of these isomer» had to be deter- 

 mined. Mr. van den Arend obtained the subjoined figures: 



°/ 2-NO,-4-Cl-toluene Initial solidifying End solidifying 



point point 



100.0 -f 38V2 



57.0 -f 9 D .7 7°.9 



44.7 -f 1°.4 -8V2 



34.8 6°.3 

 29.8 7°.2 



24.! — 4°.l — 8°.2 



17.5 0°.o 



14.1 + 0°.4 

 6.6 + 4°. 5 

 0.0 (100% 3-NO,- -f 5°.8 



4-Cl-toluene) 



Of these the following figure is the graphic representation. 



For the sp. gravities of both isomers and for some of their mixtures, 

 Mr. san den Arend found the following figures, corrected for upward 

 air pressures and for the expansion of the glass of tin* pycnometer. 

 The temperature was 80°. 0. 



