454 PROCEEDINGS OP THE AMERICAN ACADEMY, 



of a sodium salt was formed. When, however, it was warmed for a 

 few minutes, a heavy white precipitate was deposited, which, after 

 beiug watched with a little methyl alcohol, dissolved completely in 

 water, giving a clear solution. The addition of an acid to this solu- 

 tion produced a turbidity, which soon developed into a white precipi- 

 tate, undoubtedly the hemiacetal, but this passes so easily into a red 

 quinone derivative that we have not attempted to analyze it, especially 

 as its properties leave no doubt as to its nature. It follows from these 

 observations that the stability of the hemiacetals is increased by the 

 number of negative radicals, such as chlorine atoms, present. 



Action of Sodic Ethylate on Quinone. 



Although the results described in the last section made it probable 

 that the hemiacetal derived from quinone itself would be very unstable, 

 we have tried some experiments on the action of sodic ethylate on 

 quinone (0611402), and think it best to give a preliminary account of 

 them here, in spite of the fact that they have not led as yet to any 

 definite result. They have, however, proved that sodic ethylate acts 

 on quinone, but have by no means convinced us that the product is a 

 hemiacetal. On treating quinone dissolved in ether with an alcoholic 

 solution of sodic ethylate, a heavy flocculent dark green precipitate is 

 formed, which is insoluble in ether, but dissolves in alcohol or water 

 with decomposition. This precipitate does not seem to be homo- 

 geneous, as by fractional precipitation products were obtained unlike 

 in color, and also in their composition, as shown by analysis ; more- 

 over its study is rendered difficult by the fact that it takes fire spon- 

 taneously when dried at ordinary temperatures in the air ; if, however, 

 it is dried in an atmosphere of hydrogen, it can be exposed to the air 

 without taking fire at ordinary temperatures, but, if warmed to 40°, 

 it begins to glow, and burns like tinder. Before studying this rather 

 unmanageable substance further, we tried to get some idea of the way 

 in which the reaction ran by a quantitative study of it, based upon the 

 fact that all the quinone can be removed from its ethereal solution by 

 the sodic ethylate. 



In the first trial, it was found that one gram of quinone required 

 0.2352 gram of sodium for complete precipitation. 



In the second trial, one gram of quinone required 0.2460 gram of 

 sodium. 



In the third trial, 3 grams of quinone required 0.6 gram of sodium. 



These results indicate that each molecule of quinone acts with only 

 one molecule of sodic ethylate, as the amount of sodium needed in this 



