ISOMERIC CHANGE 625 



(CH 3 ) 3 C . CH \ /OH (CH 3 ) 3 C . CH 2 \ 



>C< ^ >C = CH 2 



CH 3 / \CH 3 CH/ 



Tertiary isodibutol Isodibutylene 



(CH 3 ) 3 C . CH,\ (CH 3 ) 3 C . CH, X 



•Tt >CH . CH 2 . OH -> >CH . COOH 



CH 3 / CH 3 / 



Primary isodibutol Octylic acid 



The remaining oxidation product was a ketone, C 7 H 14 0, 



which was oxidised by a stronger chromic acid mixture to 



acetic acid, 



CH 3 . CO . OH, 



and trimethylacetic acid, 



(CH 3 ) 3 C . CO . OH 



and was therefore formulated as — 



CH 3 .CO.CH 2 .C(CH 3 ) 3 . 



The ketone was evidently produced from the define 



CH 



> C . CH 2 C(CH 3 ) 3 



CH 2 / 



by oxidation of the = CH 2 group, and indicated the presence ol 

 this new hydrocarbon in the oxidising mixture. 



The complete equilibrium established by means of sulphuric 

 acid acting on isodibutol or on isodibutylene may be represented 

 by the scheme — 



CH 3 CH 3 CH 3 CH CH 3 CH 2 CH 3 CH 2 OH 



\/ \/ \ // \/ 



C C.OH C CH 



II <£— <_ <_ I 



CH CH, CH 2 CH, 



I I I I 



C(CH 3 ) 3 C(CH 3 ) 3 C(CH 3 ) 3 C(CH 3 ) 3 



Isodibutylene Isodibutol Isomeric olefine Isomeric alcohol 



At ordinary temperatures the proportion of hydrocarbon would 

 be very small, and the main action would be an equilibrium 

 between two alcohols through the intermediate olefine, 



C(CH 3 ).,.OH rC(CH 3 ) = CH 2 -i CH(CH 3 ). CH 2 . OH 



CH 2 - C(CH 3 ) 3 LCH 2 . C(CH 3 ) 3 J CH . C(CH 3 ) 3 



Isodibutol Isomeric alcohol 



At high temperatures, on the other hand, the two olefines would 



