do 



the whole then dried over anhydrous Na2So4 and filtered. 

 3,950 g. of fruits gave 983 g. of oil of a pale yellow colour and 

 with a strong turpentine-like smell. 



The ester value obtained by two hours' boiling with JN 

 alcoholic potash was 85, corresponding to 2'9 per cent, of 

 bomyl or geranyl acetates, and after acetylation this figure 

 rose to 1214, indicating the presence of about 1 per cent, of 

 free alcohols calculated as CjoH^^O. 



Determinations of density and specific rotation gave the 

 values : — 



D}.^=8674 and [(X]d,3= —19-3°. 



These values are at variance with those attributed to the 

 fruit oil of C. verrucosa by Baker and Smith, as the following 

 comparisons show : — Baker and Smith 



Fonud. (Pines of Australia, p. 106). 



D|^=-8674 (^)D'-=:-8608 



[«;']ni3 = -19-3° [(x]„=+-3" 



Esters = 2-9 % Esters = 178% 



Alcohols = 1 % Alcohols = {lj 



Yield = 2-49 % Yield = -44 % 



A careful fractionation of 82 g. of the oil under 18 mm. 

 pressure gave the following results: — 

 53-55° 55-60°' 60-70° 70-80° 80-90° 90-100° 100-135° Residue 



1. 62-3 g. 10-4 g. 2-2 g. — — . — "5-3 g. — 

 53-55° 55-60° 60-80° 80-110° 100-130° Residue 



2. 66-3 g. 6-8 g. 1-6 g. 1*1 g. 3*4 g. — 



3. 69-8 g. 3-2 g. 1-6 g. 1*1 g. 3'4 g. Slight resinous residue 



Fraction 1, 53°- 55° C, constituting 85 per cent, of the 

 total oil, had D;^=-8574 and [(x].nio= -27*44°, and these 

 constants, together with the boiling point, left little doubt 

 that pinene was the chief constituent of the oil ; to confirm 

 this the nitrosochloride and nitrol-benzylamide were prepared. 



10 g. of the fraction with 10 g. of amyl nitrite were cooled 

 to —5^ and 3 cc. of concentrated hydrocliloric acid slowly 

 dropped in with continual stirring ; separation of the nitroso- 

 chloride began after the first few drops had been added and 

 the addition occupied one-quarter hour. 



The freezing mixture and reaction product were allowed 

 slowly to attain the atmospheric temperature (two hours), and 

 the precipitate was then filtered at the pump and thoroughly 

 washed with alcohol until snow white ; after solution in chloro- 

 form and precipitation with methyl alcohol, the compound 

 melted sharply at 103° C. 



(1) Corresponding to the corrected value D'^ = 8672. 

 D 



