106 



H. G. SMITH. 



(CH 3 ) 2 C- 



-C(CH 3 )-OH 2 



COOH COOH COOH 



as was first suggested by Bredt 1 who represented camphor, cam- 

 phoric acid and camphoronic acid as follows: — 



CEL 



CH- 



I 



CEL 



CH 2 — CH-COOH 



I 



C(CH 3 ) 2 



I 

 CH 2 — C(CH 3 )-CO 



Camphor. 



COOH 



CH, 



C(CH 3 ) 2 



I 

 CH 2 — C(CH 3 )-COOH 



Camphoric acid. 



COOH 



I 

 C(CH 3 ) 2 



I 

 C(CH 3 )-COOH 



Camphoronic acid. 



Eudesmol does not form the intermediate acid (camphoric acid) 

 on oxidation with dilute nitric acid, but camphoronic acid, again 

 indicating that the molecule of eudesmol differs from that of 

 camphor. If we consider eudesmol to be in agreement with Briihl's 

 formula for eucalyptol, the camphoronic acid derived from it would 

 require to be depicted as isopropyltricarballylic acid. 



If we accept Bredt's formula for camphoronic acid to be 

 trimethyltricarballylic acid, and which formula is supported by 

 the synthetical production of Perkin and Thorpe, then Briihl's 

 formula for eucalyptol cannot be considered to be correct, and 

 eudesmol will require to be constructed in a form corresponding 

 somewhat with Bredt's formula for camphor, but with the oxygen 

 atom attached to more than one carbon atom, as follows : — 



CH. 



CH 



OH 



H 



Eudesmol. 



1 Ber. 1893, xxvi., 3049. 



