206 



SCIENCE 



[N. S. Vol. LII. No. 1339 



The next meeting will be held in Convocation 

 Week, December, 1920, at Chicago. 



Charles F. Brooks, 



Secretary 

 Weather Bdeeau, 

 Washington, D. C. 



THE AMERICAN CHEMICAL SOCIETY. 

 Ill 



The Kaufler-Cain formula for diphenyl deriva- 

 tives: Oliver Kamm and C. S. Palmer. 



BB'-dichlorodiethyl ether: the oxygen analogue 

 of mustard gas: Olivee Kamm and J. H. Waldo. 

 The chlorination of a-cetone : A. W. Homberger 

 and M. Borries. Technical acetone was purified 

 and treated with dry chlorine in sunlight. During 

 the chlorination three distinct steps were noted. 

 The first step was completed at the close of the 

 first half hour. No hydrochloric acid was liber- 

 ated during this stage. The second step lasted two 

 hours. The heat of reaction was much higher than 

 in the preceding step and whenever the tempera- 

 ture rose over 80 degrees violent reaction, result- 

 ing in flames, took place. A third step took place 

 after this second reaction with no violent action 

 and a temperature maintained itself below 80 de- 

 grees, and no tendency to burst into flames. Dur- 

 ing the second and third step hydrochloric acid was 

 liberated, much more during the second than the 

 third step. The resulting liquid of chlorination 

 ,waa submitted to distillation under diminished 

 pressure and three distinct fractions obtained. 

 The three fractions, when redistilled, showed 

 definite and well-defined boiling points and prop- 

 erties. Each of these products is being investi- 

 gated at present. 



The use of a chart in the study of organic chem- 

 istry: Chas. W. Cdno. The studies are divided 

 into three great divisions, the memory studies, the 

 reasoning studies, and the constructive studies. 

 The two great memory studies are history and the 

 languages. History concerns itself with data and 

 dates, or to put it abstractly, with sequence and 

 facts. Language concerns itself with interpreta- 

 tion. If we examine the reasoning studies such 

 as chemistry we find they have a language and 

 sequence and data that need to be made a part of 

 the memory before the student can very well rea- 

 son intelligently. In organic chemistry the lan- 

 guage is exceedingly difficult and the data and se- 

 quence very voluminous. The use of a chart such 

 as the one published by the author has its use, 

 therefore, to help the student in acquiring the 



data, sequence and language of organic chem- 

 istry. 



The mechanism of some reactions involving the 

 Grignard reagent: Hbnrt Gilman. It has been 

 conclusively proved that the reactions of ketones 

 are not restricted to primary addition to the 

 ethylenie linkage. The benzoate of triphenyl- 

 vinyl-aleohol was obtained when the addition com- 

 pound of diphenyl ketene and phenyl magnesium 

 bromide was treated with benzoyl chloride. The 

 Grignard reagent, therefore, has added to the car- 

 bouyl group. Preliminary experiments on the 

 mode of reaction of the Grignard reagent and 

 phenyl isocyanate (and phenyl iso-thiocyanate) , 

 indicate the following: first, but one molecule of 

 phenyl magnesium bromide adds; second, addi- 

 tion takes place on the carbonyl (and thio-oar- 

 bonyl) linkage; and, third, addition is probably 

 restricted to this linkage, as with the ketones. 



The nitration of certain halogenated phenols: 

 L. Chas. EAiroRO. In preparing halogenated 

 o-aminophenols with which to test further the mi- 

 gration of acyl from nitrogen to oxygen (J. A. C. 

 S., 41, 2068 (1919)), several of the brominated 

 cresols were nitrated according to the method used 

 by Zincke (J. pr. Chem. (2), 61, 561 (1900)), who 

 found that in the meta series the halogen atom 

 para to hydroxyl was replaced by the nitro group, 

 while in the ortho and para series the atom ortho to 

 hydroxyl was replaced. In none of these cases 

 did he report the formation of isomeric nitro 

 compounds in a single experiment. In the present 

 work it has been found that the dibromo and tri- 

 bromo-ortho cresols, to which Zincke has assigned 

 the structures 



CHa CH, 



i^OH i^OH 



Br 



\/ 



Br 



Br 



Br 



Br 



both give isomers when they are nitrated as indi- 

 cated above. The structures of the isomers, as 

 well as the mother substances, are under consid- 

 eration. 



Action of aromatic alcohols on phenols in the 

 presence of aluminum chloride: Ealph C. Huston. 

 Earlier work has shown that aromatic alcohols (pri- 

 mary or secondary) are readily condensed with aro- 

 matic hydrocarbons such as benzene, toluene, etc., 

 to form diphenyl methane or derivatives thereof. 

 In the present work benzyl alcohol was allowed to 

 react at relatively low temperatures with phenol in 



