164 PROCEEDINGS OF THE AMERICAN ACADEMY 



hydrogen at all, but ascribe it rather to the action of the sodium itself, 

 as if in the presence of an inditferent liquid (Baubigiiy's reaction). 



It is to be remarked, however, that they have confined their atten- 

 tion to the reduction of camphor by sodium and alcohol, and were not 

 justified in thus rejecting our reaction, 



C,JI,,0 + H, = C,„H,,0, 



as they had not repeated the experiment described in the beginninif of 

 our paper, in which 25 g. of camphor by the action of an excess of 

 sodium and moist toluol were completely converted into borneol, as 

 shown by the melting-point 197-198°, and a combustion. Tiiat this 

 observation, and therefore the reaction given above, are correct, has 

 been proved by Immendorff under the direction of Anschutz, who has 

 published a most welcome paper * on the sul)ject in the interval be- 

 tween the appearance of Kachler and Spitzer's paper and this answer, 

 which has been much delayed, because, since the publication of their 

 pa]Der, I have had no laboratory at my disposal until lliis autumn. 

 Immendorff's proof consisted in increasing the amount of sodium used 

 upon the alcoholic solution of camphor from \l^ to 3^- times the the- 

 oretical amount, when he obtained a product, which, after crystalliza- 

 tion from petroleum ether or sublimation, melted at 199-200°, and 

 was proved to be pure borneol by analyses of its chloride. Although 

 in this way he confirms our theoretical views, he did not obtain better 

 results from our practical process than Kachler and Sjiitzer, as he got 

 as low a melting-point (181°) as they, when he used the amount of 

 sodium recommended by us (IJ times the theory), and even with twice 

 the theoretical amount did not get a melting-point above 188°. As 

 we had got a melting-point of 193° for the crude product, 1 felt that 

 it was advisable to take up the subject again, and study the conditions 

 of the reaction more carefully, especially as both Kachler and Spitzer 

 and Immendorff dwell on the interest of this process from a theoretical 

 as well as a practical point of view. 



The result of my experiments is, however, that, even when in fol- 

 lowins: our oriixinal directions I tried to make the conditions as unfa- 

 vorable as possible, the melting-point of the crude product was 187-188°, 

 and in other repetitions 188° and 189°, so that my products with one 

 and a third times the theory of sodium melted 6° to 8° higher than the 

 corresponding ones of Imniendorflf, and as high as his with twice the the- 

 ory,! but not so high as our previous melting-point of 193°. Although, 



* Ber. d. ch. G., xvii. p. 103G. 



t Witli twice the theory I obtained melting-point 194°. 



