624 SCIENCE PROGRESS 



tertiary butyl alcohol. Its main oxidation products were acetone 

 and trimethylacetic acid, 



CH 3 \ CH S \ 



}C = O and CH 3 _^ C . CO . OH 

 CHS CH S -^" 



and its constitution was therefore — 



CH 3 \ / CH 3 



>C = CH.C^— CH S 



CH/ \ CHa 



a structure that could be accounted for on the view that the 

 actual condensation took place between a molecule of the 

 tertiary alcohol and a molecule of isobutylene derived from it 

 by the removal of water. 



CH 3 \ / CHs CH3\ / CH 3 



V .-CHUHO; C^-CH, -» \C=CH.C^—- CHs 



CH 3 / \CH. CH3/ 



CHs 



This structure was confirmed by combining the hydrocarbon 

 with hydriodic acid, and hydrolysing the iodide by means of 

 moist silver oxide. The product, " isodibutol," had the com- 

 position indicated by the formula C 8 H lg O, and showed all the 

 properties of the tertiary alcohol HO . C(CH 3 ) 2 . CH 2 . C(CH 3 ) 3 , 

 including a marked stability towards oxidising agents. When 

 the oxidation was forced by using a concentrated acid mixture, 

 the products of the action were the unchanged alcohol, isodi- 

 butylene — formed by the dehydrating action of the sulphuric 

 acid — and oxidation products derived from it : no direct oxida- 

 tion of the alcohol could be detected. The experiments served, 

 however, to show that the interconversion of olefine and tertiary 

 alcohol, noticed in the case of butylene and amylene, took place 

 also in the case of isodibutylene, and a more detailed study of 

 the oxidation revealed the presence of an even more complex 

 equilibrium involving not only two isomeric alcohols, but two 

 isomeric olefines. 



An oily acid left behind after the distillation of the trimethyl- 

 acetic acid proved to be an octylic acid of the formula C 8 H 16 2 , 

 and the conditions of its formation left no doubt that it was the 

 analogue of the isobutyric acid obtained as a by-product in the 

 oxidation of tertiary butyl alcohol, and that its formation was 

 due to a similar series of changes as set forth below : 



