OM THE CONSTITUTION OF CAMPHOR. oU5) 



(b) Oxidation of Camphoric Acid loith Diltde Cold Permanganate. 



When camphoric acid, dissolved in the requisite quantity of soda, is 

 allowed to remain with cold dilute potassium permanganate solution foi 

 some months, it is converted into a dibasic acid having the formula 

 C8Hi20,5 or C(;H[oO (C00H)2 and oxalic acid, the products being in 

 approximately equivalent amount. This acid yields only additive pro- 

 ducts with hydroxylamine or hydrazines, so that the lifth oxygen atom 

 does not possess true ketonic functions. On reduction it yields, first, a 

 lactonic acid, CgHioO^, and then <i/J/3-trimethylglutaric acid. 



Balbiano explains the behaviour of the acid CgH,20.;; on the assump- 

 tion that it is an acid possessing the structure of an oxide derived from 

 a dihydroxy acid 



COOH . CMe . CMeo . CH . COOH, 



\o/' 



and it Is not easy to understand what other view can be taken. The 

 successiA'e stages of its reduction are consequently 



CMe . COOH CMe . COOH CHMe . COOH 



l-_ \_ J 



CMe2)0 -> CKe^^0{1) -> CMe 



2 



CH. COOH CH, . CO CH, . COOH.^ 



2. The Products obtained by eliminating a Carboxyl Group 

 FROM Camphoric Acid. 



(a) Electrolysis of the Isomeric Ethyl Tlydruyen Camphorates, 



When the two isomeric ethyl hydrogen camphorates (compare C. 1. b.) 

 are submitted to electrolysis the products consist for the most part of 

 esters of unsaturated, ciosed-chain, monobasic acids, pi'oduced in accord- 

 ance with the equation 



C,H,,<coOH =^°2 + H2-f-CsH,3 . COOEt. 



(i.) Electrolysis of Ortho-ethyl Hydrogen Cainphorate. — Ortho ethyl 

 camphorate (C. 1. b.) on electrolysis yields mostly the esters of two 

 isomeric acids, namely, campholytic and isolauronolic acids. These two 

 acids are inactive, and are intraconvertible by processes analogous 

 to those whereby fumaric and maleic acids may be converted one into the 

 other.* 



' Balbiano, Ber., 27, 2183. 



- Compare also Balbiano, Ber.. 28, 1506; Atti Luicei, 1894, i. 278, and ii. 240; 

 Gaaetta Chhn. Ital., 26, 1; and Ber., 30, 289 and 1901. Also Mahla and Tiemann, 

 J9rr. 28, 2151 and 2811. 



' Walker, Trans. Client. Soc, 63, J 93, and 67, dil. . 



