104 JOUKNAL OF THE MiTCHELL SoCIETY [April 



figures were obtained for a pure phenjlsemicarbazone, althougli 

 a good figure was obtained for carbon. Tbe hydrogen persisted 

 in being 0.6 to 0.8 per cent too bigb. It is not surprising that 

 pbenylsemicarbazine sbould cause a reaction in solutions of 

 botb the yellow and the red forms since in solution both enol and 

 keto-forms exist simultaneously. A further study of this ques- 

 tion is under way. 



Bromination of Tetrahydroxynaphthalene 

 According to Meyer enol forms react instantaneously with 

 bromine whereas saturated keto-forms do not. The constitution 

 of tetrahydroxynaphthalene complicates this reaction because the 

 bromine may not only act upon the four hydroxyl groups present 

 but also upon the four hydrogen atoms in the nuclei. We made 

 four comparative experiments using 1, 2, 3 and 4 molecules of 

 bromine respectively for one molecule of the tetrahydroxynah- 

 thalene. Saturated glacial acetic acid solutions of both sub- 

 stances were used and the reactions were started at 10°. l^o 

 reaction was apparent at first in any case but on standing at 

 room temperature over night masses of crystals appeared in 

 every case. The results are briefly stated as follows : I. 0. 5g 

 substance -\- 0.47g Br. Product, black crystalline mass, 0.46g. 

 Sublimes at 260° without melting. II. 0.5g substance + 0.94g 

 Br. Product, red crystals, 0.63g. Sublimes at 160-200°. III. 

 0.5g substance -\- 1.41g Br. Product, reddish orange crystals, 

 0.78g. Sublimes at 150-240°. Melts at 240-252°. IV. 0.5g 

 substance + l.BSg Br. Product, yellowish orange crystals, 

 0.56g. Melt at 168-174° and decompose above 174° to a dark 

 red liquid. The last product appears to be the purest but there 

 is a decided falling off in the yield. The reaction will be studied 

 further in this laboratory. 

 Chapei. Hill, N. C. 



