﻿74 BACON AND FREER. 



The above results confirm the previous work in every way and estab- 

 lish the fact that the action of sodium on acetone gives a sodium 

 derivative which can only be sodium acetone. 



In view of the above conclusions it is not deemed necessary further 

 to discuss Miss Taylor's results as, apparently, she had not reproduced 

 the conditions under which Freer worked. A very short review of some 

 of the chief facts established in the earlier literature and which Miss 

 Taylor appears not to have considered may not be out of place, as 

 it will serve to recall some of the arguments which were not discussed in 

 Miss Taylor's paper. The portion of the product of the action of sodium 

 on acetone which is insoluble in ether was shown by Freer 10 to consist 

 of acetone sodium, sodium isopropylate, and disodium pinakonate, the 

 soluble portion, of a sodium derivative of acetone, no sodium isopropylate 

 was isolated from this soluble portion and, if it is not carefully acidified, 

 mesityloxide and phoron are to be obtained. In studying the products 

 of the action of chlorcarbonic ether on sodium acetone, Miss Taylor sug- 

 gests that a mixture of ethyl isopropyl carbonate and diethylcarbonate 

 would yield 34 per cent of carbon dioxide, whereas Freer found 33.89 

 per cent on decomposing the oil boiling between 128° and 129° and pro- 

 duced by the interaction of sodium acetone and chlorcarbonic ether 

 (calculated CO, for C c H 10 O 3 , 33.84 per cent), but Miss Taylor ap- 

 pears to have overlooked the statement X1 that Freer also proved the 

 presence of ethyl alcohol and acetone in the products left after sapo- 

 nification. If acetone had been present as mesityl-oxide, the percent- 

 age of carbon dioxide would have fallen very much. It was further 

 shown by Freer that the fraction boiling at 128° 12 yielded a sufficient 

 amount of acetone on decomposition with dilute acid to allow of its 

 being separated as the acetone sodium-bisulphite compound. (Found 

 carbon dioxide 33.7 per cent; the quantity of ethyl alcohol was less than 

 one-half the organic liquid isolated, it boiled at 78°.) We would, there- 

 fore, if we were dealing with a mixture of diethylcarbonate, ethyl isopropyl 

 carbonate and mesityloxide, need to assume a large proportion of the 

 latter substance to be present, and this would inevitably have lowered 

 the carbon dioxide' very markedly. Furthermore, the oil boiling between 

 132° and 137° yielded 30 per cent of acetone (calculated, 48.8 per cent) 

 and this figure, because of the difficulties in quantitative estimation, is 

 undoubtedly too low. It does not seem reasonable to assume that an oil 

 which would contain a sufficient quantity of mesityloxide to yield so 

 much acetone would not further react with phenylhydrazine, but on the 

 other hand this percentage would correspond to a total of 62 per cent 



10 Amer. Chem. Journ. (1893), 15, 592. 

 ™Ibid. (1891), 13, 325. 

 12 Ibid. (1895), 17, 11. 



