;]20 



REPORT — 1000. 



be an ((-bromo-acid. These facts are readily explained by Bredt's, but 

 not by the Perkin-Bouveault formula, as in accordance with our ordinary 

 views the latter formula would make a-bromocamphoric acid a (3- and not 

 a y-bromo-acid. 



COOH CH, -CBr . COOH 



/CBr 

 CH2 CMsa 



CH2 



I 



-CBr 



I 



CH,/ 



\ / 

 CMe 

 Bredt. 



COOH 



CH2 CMe . COOH 

 CMso 



Perkin-Bouveault. 



That the position of the bromine atom in the nucleus represents the posi- 

 tion of attachment of the lactonic oxygen atom is shown by (1) the fact 

 that diethylbromocamphorate when heated yields ethyl Ijromide and 

 ethyl camphanate 



CBr C— O 



: -^ • I + EtBr 

 C.COOEt C— CO 



(2) that camphanic acid on treatment with phosphorus pentachloride (or 

 pentabromide) regenerates ordinary chloro- (or bromo-)camphoric chloride 

 (or bromide) ; a fact of which the author has convinced himself. 



C— O C.Cl 



c.co 



I + PC15 



C . CO.Cl 



+ POCK 



That camphanic acid does not contain the grouping 



CH. O 



: I 

 C — CO 



receives support in the fact that it is obtained by oxidising camphoric 

 acid with chromic acid, and in accordance with the researches of Fittig 

 such an oxidation occurs only at the tertiary carbon atoms. 



(f ) T/ie Formation of jBalb{ano'» Acid and O.ialic Acid iu approxi'irmtehj equivalent 

 Amount hy the Oxidation of Camphoric Acid (compare E. 1. h.). 



The formation of an acid having the constitution given by Balbiano for 

 the product CgHi^Oj is readily interpreted by the use of Bredt's formula 

 as follows : — 



CH COOH 

 COOH / 1 



CH . COOH 



I 

 CMea 



COOH 



+ O CMe, 



\ 



CMe . COOH 



CMe . COOH 



tJsing the Perkin-Bouveault formula, the course of the change becomes 

 Very difficult to understand, and must necessitate the assumption that 0, 



