

Found 

 (percent) 



CI 



20.71 



Mg 



12.8 



60 BACON. 



The iiisoliihlc porlion: One and four-tenths grams of the solid remaining under 

 ether was removed, washed witli absolute ether, dried rapidly on a porous plate, 

 weighed to a tentlr of a gram and thrown into water. Xlie substance proved to 

 be exceedingly unstable in tlie air, the yelloAv powder soon Ijecoming very hot, 

 witli tlie separation of a red oil, a behavior similar to that of sodium acetone, 

 • while at the same time a very marked odor of benzaldehyde is developed. The 

 powder dissolved rather slowly when thrown into water so that it was necessary 

 to add a little dilute sulphuric acid. The aqueous solution was extracted twice 

 with small quantities of ether, the solvent allowed to evaporate slowly in the air 

 and a crystalline body, which melted at 121° and which proved to be benzoic acid 

 was separated. A very small amount of an oily residue, having the odor of 

 benzaldehyde remained. Magnesium and chlorine determinations were made on 

 aliquot portions of tlie aqueous solution with the following result: 



Calculated (per cent) tor 

 H 

 CoHjCOMgCl CoH5C<9'^J'^' 

 21.5 11.2 



14.7 7.9 



These figures, considering the method used and the diiBcultj' of wash- 

 ing out all free benzaldehyde and the certainty of some oxidation during 

 the transfer, agree very well with those calculated. 



The remainder of the solid was heated for three hours on a reflux condenser 

 with 18 grams of benzoyl chloride. The produ^ct was then treated witli alkali 

 and the neutral part, on distillation, gave 4 grams of benzaldehyde, 1 gram of a 

 solid, mostly benzoic acid " and 5 grams of tarry residue. From tlie alkali 25 

 grams of benzoic acid were recovered, it is therefore evident that the solid addition 

 product does not react with benzoyl chloride. 



Experiment 10. — There were used 10 grams of limonene hydrochloride, 3 grams 

 of magnesium and 40 cubic centimeters of absolute ether. The apparatus was 

 arranged as follows: Flask No. 1 in which the Griguard reaction took place, was 

 fitted with a reflux condenser and a filter tube running to fiask No. 2; in this 

 second flask, which also carried a reflux condenser, the filtrate from No. 1 was 

 treated with benzaldehyde, and a second filter tube delivered the filtrate from 

 No. 2 after this reaction, into flask No. 3. All parts were arranged so that they 

 could constantly be kept filled with dry hydrogen. After the Grignard reaction 

 was completed in No. 1, the filtrate which was passed over into No. 2 was treated 

 with benzaldehj'de and the solid substance which was formed was well washed with 

 absolute ether, all soluble portions and washings being sucked over into No. 3. 

 On final analj'sis No. 3 was found to contain no magnesium and only C,oHis, and 

 the excess of benzaldehyde. The solid in No. 2 was placed under benzene (dried 

 by distilling over sodium wire) and dry oxygen was run into it for eight hours. 

 The reaction is not very marked, this result possibl.y being due to the fact that 

 the solid forms dense cakes, dilficult to penetrate. However, a gradual reddening 

 took place so that the whole, when the current of o.xygeii was finally shut oft' had 

 assumed a deep red color. There resulted 1.4 grams of benzoic acid melting at 

 121°; 0.9 grams benzaldehj'de proved by transference into the phenylhydrazone 

 melting at 155° and 1.2 grams of tar. Magnesium and chlorine determinations 

 were made and when calculated on the total substance finally obtained, gave the 

 numbers 11.8 per cent for magnesium and 20.4 per cent for chlorine. Calculated 

 for C„H.,C'OMgCl, magnesium 14.7 chlorine 21.5 per cent. 



" Benzaldehyde oxidizes very rapidly in this hot, moist climate. 



