The lower boiling fraction and the residue were discarded. The second 

 fraction, 100-101 C. at 10 millimetres, gave the following results : 



Boiling point (766 mm.) : 218-220 C. (corr.) 



Specific gravity at 15 C. ... ... ... ... = 0-9359. 



Rotation a v ... ... ... ... ... ... - - 5-0 C. 



Refractive index at 20 C. ... ... ... ... = 1-4816. 



Nitrosochloride, melted at ... ... ... ... 113 C. 



Phenylurethane, melted at ... ... ... ... 112 C. 



Both the nitrosochloride and the urethane were readily formed and in good 

 quantity. These results indicate that the alcohol was terpineol and that the 

 laevo-rotatory modification predominated to a small extent in the oil of this species. 

 The portion boiling between 101-110 C. was again fractionated at 10 

 millimetres, when 30 c.c. were obtained boiling between 108-110 C. This 

 fraction had a distinct odour of geraniol. The specific gravity at 15 = 0-9316; 

 rotation a D 1-5; refractive index at 20 = 1-4841, and yielded a good amount 

 of a urethane, melting at 112. It is thus evident that a considerable amount of 

 terpineol was also present in this portion. That it also contained geraniol was 

 shown by the formation of citral on oxidation. 



That geraniol is a common constituent in the oil of E. Australians is also 

 suggested from the frequent presence of citral in the natural oil, and we have 

 isolated this aldehyde in a pure condition from the oil of this species distilled from 

 material growing in the Burraga district of New South Wales. 



Terpineol was also prepared from the second and third hour oils of this 

 species, distilled from material growing at Nerrigundah, New South Wales. 500 c.c. 

 boiling above 190 C. were repeatedly fractionated at 10 millimetres pressure, 

 the following fractions being eventually obtained (temperatures uncorrected) : 

 Boiling between 70 and 99 C., amount was 180 c.c. 

 99 101 C., ,, 144 c.c. 

 ,, 101 104 C., ,, 5 c.c. 

 105 ,, 109 C., 30 c.c. 

 no 115 C., ,, 40 c.c. 

 The fraction 99-101 C. at 10 millimetres had : 



Specific gravity at 15 C = 0-9362. 



Rotation a D ... ... ... ... - 3'$ 



Refractive index at 20 C. = 1-4816. 



Nitrosochloride melted at 113 



Nitrolpiperidine ,, 159-160 



Phenylurethane ,, ... 112. 



When shaken with 5 per cent, sulphuric acid a good yield of terpin hydrate 

 was eventually obtained. 



The fractions 101-104 and 105-109 gave results agreeing with those 

 of the first sample, and geraniol was readily detected in the higher-boiling 



fraction. 



The terpineol from the Nerrigundah oil was thus in agreement with that 

 from the Youri material, although showing a slightly less laevo-rotation. There 

 was, however, a difference of four years in the dates of distillation of the two 

 samples. This species is probably the best of all the Eucalypts from which to 

 distil an oil containing the maximum amount of terpineol. 



