( 661 ) 



of n acid corresponding with 0.82 millimols of meta if we apply tlie correc- 

 tion of 2.6»^ foi' the meta compound attacked. 0.82 millimols = 10.5% 

 of the meta compound. 



h. 1.1250 grams = 7.98 millimols. of the said mixture were treated in 

 an analogous manner with the equivalent quantity (16.9 cc.) of njo-u 

 sodium methoxide. The liquid was then titrated back with 0.85 cc. of fi acid, 

 corresponding, after applying the correction, with 0.87 millimols. of the meta 

 compound, or 10.9 %. Taking the mean of these two experiments we find 

 10.7 "/„ of the meta-compound. 



l)r. 1)KF,KMAN had ohsei-vcd that heiizene dijiitroHuoi-idc (Fl : NO.^ : 

 N( ).^ = J : 2 : 4) is converted at 15° in a few minutes into the corre- 

 sponding' anisol l»y the action of sodium methoxide. This circum- 

 stance miglit he taken advantage of for the quantitative deterniMiation 

 of tiiis dinitro compound in the presence of benzene yMiitrotluori(ic 

 if the latter should suffer no change. This Avas, indeed, the case : 



1.0035 grams of the para compound were treated at 15" for 5 minutes 

 with 9.58 cc. of /^Vgi = ^ ^^- '^ sodium methoxide. After being poured into 

 water the liquid was titrated back with 5 cc of n acid. 



A mixture of tJie two gave the following result: 



1.1680 grams of a mixture containing 10.9% of the dinilro compound were 



digested at 15" for 5 minutes with 17.6 cc. of n/.^.i.^ Na OCH^. The liquid 



was then titrated back with 7.6 cc. of n acid; there was, therefore, present 



17.6 

 a quantity of dinitro compound of — ^- — 7.6 = 0.7 millimols , or 0.1302 gram 



corresponding with 11.1 % of the dinitro compound. 



The above observations rendered it possible to quantitatively deter- 

 mine any I)enzene di- or metanitrotluoride eventually present in a 

 nitration product of benzene fluoride. In order to determine the 

 benzene orthonitrofluoride contained therein, I converted this into the 

 dinitrocompound by renewed treatment of the nitration product willi 

 concentrated nitric a(!id. Dr. Beekman had found that a further nitra- 

 tion took place (as shown by the increased sp. gr.) AvJien the said 

 product was treated for half an hour at 0° with five times its weight 

 of nitric acid of 1.52 sp. gr., but that e\en after this treatment, 

 traces of benzene ortlionitrofluoiide may still be detected by boiling 

 the compound with aqueous sodium hydroxide which yields o-nitro- 

 plienol. On the other hand Dr. Hkkkman showed that pure benzene 

 /)- and ///-nitroMuoride are t(uite unaffected by this renewed treatment. 

 In oi'der lo get a fui'ther and complete nitration of tlie ortho 

 compound. 1 |)i-oh)nged the lime of the renewed treatment with 

 nitric acid lo one hour after first ascertaining whether benzene 



44* 



