Aqc 



-CH 



I 

 CH 2 



— 189 — 



2 (H 3 C) C — CH - CH 2 2 (H S C) C 

 + H2O 



HOCH-C(CH 3 )-CH 2 



Fenchyl alcohol. 



FfeO 



CH 



I 



CH 2 



CH 2 



H 2 C — C(CH 3 )CHOH 



Jsofenchyl alcohol. 



,(H,C)C- 



CH 



I 

 CH 2 



-CH 



I 

 CH S 



+ 

 CH 2 



+ C-CH, 



/?-Pinolene. 



CH 2 2 (H 3 C)C — CH C0 2 H 2 (H 3 C)( 



CH 2 +!° 



C(CH 3 )C0 2 H H 2 C — C(CH 3 )CO 



Zsofenchone. 



CO-C(CH 3 )CH 2 



Fenchone. 



H 2 C 



Jsofenchocamphoric acid 



It would lead us too far to give an explanation of the formation of 

 the fenchene compounds from pinene and of the author's theory of the 

 formation of geometric isomerides in the bromination of dibasic alicyclic 

 acids with hydrogen in the a-position, and in the re-substitution of the 

 a-bromoderivatives. Nor are we able to enter into further details of the 

 rich experimental material. 



On the reduction of pulegone, see p. 183. 



Car von e. When molecular quantities of hydrogen cyanide and car- 

 vone are allowed to react at ordinary temperature, the resulting product 

 is cyanodihydrocarvone 1 ), m. p. 93,5 to 94,5°; ([«] D + 13,5°). When the 

 reaction is carried out in hot alcoholic solution the result, according to 

 A. Lapworth and V. Steele 2 ), is an isomeric product, /?-cyanodihydro- 

 carvone, m. p. 84° ([«] D — 42,1°). In the presence of bases this body shows 

 the effect of mutarotation. 



When a mixture of carvone hydrosulphide and aqueous solution of 

 potassium cyanide is diluted with glacial acetic acid, the result, as shown 

 by V. Steele 3 ), is the generation of a dinitrile, with elimination of water. 

 The dinitrile has the following formula p. 190. 



It melts at 94°, and has opt. rot. [«] D12 o + 4,02° (0,4062 g. substance 

 L^ 25 cc. alcohol). When heated with ferrous hydroxide and alkali it readily 

 loses both its hydrogen sulphide and hydrogen cyanide. When heated 

 with concentrated aqueous hydrobromic acid solution, the nitrile is partly 



!) Comp. Report October 1906, 132. 

 *) Journ. chem. Soc. 99 (1911), 1877. 

 *) Proceed, chem. Soc. 27 (1911), 240. 



