824 REPORT— 1900. 



The general properties of camphoric acid are those of a glutaric acid, as its 

 In'omo-derivative at once yields a stable lactone ; a behaviour altogether 

 inconsistent with the view that it is an a-brominated succinic acid. 



The supporters of the succinic acid formula for camphoric acid have 

 raised the contention that bromocamphoric acid is a /3-brominated acid 

 containing the complex 



CHBr . CPI . COOH 



: I 



C. COOH 



c 



and in support of this advance the fact that its anhydride on treatment 

 with water or sodium carbonate loses carbon dioxide and hydrogen bromide, 

 yielding a small quantity of lauronolic acid, a behaviour certainly in 

 accordance with the view that it is a /3-bromo-acid. The necessity for 

 such an assumption, however, is in itself clearly an argument against the 

 succinic formula, since the bromination of a saturated acid in the /3-posi- 

 tion is unknown. Moreover on this assumption bromocamphoric anhy- 

 dride itself still contains an a -hydrogen atom, and should be capable of 

 further bromination, a surmise altogether at variance with the facts. It 

 is much more probable that the formation of lauronolic acid is due to an 

 idiosyncrasy of the compounds involved, and little or nothing is known of 

 the behaviour of cycloid a-bromo-acids in this respect. 



It obviously cannot be urged that the formation of lauronolic acid is 

 evidence in favour of the presence of the complex 



CH2 . CBr . COOH 



C . C COOH 

 C 



as such an acid would afford an isomer of lauronolic acid, possibly campho- 

 lytic or isolauronolic, and containing the complex 



CH., . C . COOH 



II 

 C . C 



C 



and, in fact, that it does not do so isi in 'tself evidence against the 

 succinic formula for camphoric acid. 



It may therefore be stated that the general properties of camphor and 

 camphoric acid are of a kind which should be expected were Bredt's 

 formula the correct one. 



Comparing now the weight of evidence in favour of the two formulae 

 as elicited by examination of the exact structure of the degradation pro- 

 ducts of camphor, Bredt's formula is seen to be favoured in a high degree, 

 and only the structure of isolauronolic acid and of /3-campholenic acid 

 (probably, as has been pointed out, homoisolauronolic acid) appears to 

 militate strongly against its acceptance. It is especially significant, 

 moreover, that the /3-campholenic derivatives are produced, probably in 

 all cases, as secondary products from the a -derivatives, and the behaviour 



