278 SCIENCE PROGRESS 



In the same manner acetone and ethylic alcohol give as main 

 product, trimethylethyleneglycol : 



(CH 3 ) 3 CO + OH.CH 2 .CH 3 -> (CH 3 ) 2 C(OH).CH(OH).CH, 



but isopropylic alcohol, acetaldehyde and dimethylethylene- 



glycol are also formed as follows : 



i. CH3.CO.CH3 + CH 3 .CH.,.OH -> (CH 3 ), CH(OH) + CH3.CHO 

 ii. CH 3 .CH 2 .OH + CH3.CHO -> CH, . CH(OH).CH(OH) . CH, 



The action of light on the methylic and ethylic alcohol solutions 

 of acetone is in striking contrast with its action on alcoholic solu- 

 tions of benzophenone or acetone ; in the latter case only benzo- 

 pinacone or acetopinacone are formed, by a process of reduction. 



Acetone and ethylic ether 1 give isopropylic alcohol 

 (reduction) and a compound formed by their association, 

 OH . CMe 2 . CHMe . OEt, together with other substances not yet 

 investigated. 



Acetophenone and ether 2 interact mainly in accordance with 

 the equation : 



C 6 H 5 . CO . CH 3 + (C 2 H 5 )X> -» g^ 5 > C(OH) . CH <^( Hi 



Some resin is formed but no acetopinacone, which is the 

 main product when alcohol is used in place of ether. This 

 behaviour is strikingly different from that of benzophenone 

 which gives with ether much benzopinacone (this is the sole 

 product when alcohol is used in place of ether) together with 

 the compound : 



C : g;>C(OH).CH<gE« 



Benzophenone and benzenoid hydrocarbons also interact in 

 a striking manner. When toluene is used much benzopinacone 

 is produced together with some dibenzyl ; thus 



Ph 2 .C.OH CH 2 .C 6 H 5 

 2Ph 2 CO + 2CH 3 .C 6 H 5 -> I +| 



Ph 2 C.OH CH 2 .C 6 H 5 



but a considerable quantity of diphenyl benzylcarbinol is also 

 formed : 



r u p TT 



QH? C0 + CHs • CgHs = CH^ C(OH) • CH - • CeHs 

 Exactly similar action occurs in the case of benzophenone and 

 ethylbenzene, /(-xylene and ^-cymene (in this case the carbinol 



1 Atti R. Accad. Lincei, 191 1, 20, i. 721. Compare Paterno and Chieffi, 

 Gazzetta, 1910, 40, ii. 321. 



2 Atti R. Accad. Lincei, 1910, 19, i. 645. Compare Paterno and Chieffi, 

 Gazzetta, 1909, 39, ii. 415. 



