ON THE CONSTITUTION OF CAMPHOR. 303 



on sodium camphor, or of the dehydration of the oxime of a -camphor- 

 aldehyde, must necessarily be an a-derivative. 



/CHNa /CH.CN 



C«H / I +Br.CN=aH / | +NaBr 



/CH.CH:N.OH /CH.CN 



and when this compound is boiled with alkalis it suffers hydrolysis in two 

 senses, being converted into ammonia and homocamphoric acid.^ 



/CH.CN /CH.,.COOH 



C,H / I +3H,0=CsHi / " +NH, 



^CO ^COOH 



(c) Camphor may be regenerated from Homocamphoric Acid. 



When the barium salt of homocamphoric acid is subjected to dry 

 distillation it is broken up into barium carbonate and camphor, a change 

 which must be expressed by the equation 



/CH2.CO.O. /CH 



C«Hi / >Ba=C,Hi / I +BaC03.2 



^co.o / '^co 



3. The Ketone Ring is either a 4- or a 5-Carbon Ring. 



Since camphoric acid very readily affords an anhydride on treatment 

 with acetyl chloride, even in the cold, it follows that it must be a deriva- 

 tive of succinic or of glutaric acid, so that it may be represented by one 

 of the formulae 



I 



I 



C— CAMPHOR CONTAINS THE GROUP 

 CH— CH, 



: I 



C CO 



c 



' Haller, Diisertation, Nancy, 1879. 



2 Haller, Compt. Rend., 122" 446 ; and Baeyer, Ann., 289, 6. 



