DARWINIAS OF PORT JACKSON AND THEIR ESSENTIAL OILS. 173 



using Beckmann's method. Oxidation takes place readily, giving 

 an oil with a strong lemon odour. The separated oil was agitated 

 with a solution of acid sodium sulphite, the crystalline mass 

 separated, purified, and decomposed by sodium carbonate. The 

 aldehyde thus obtained had a strong odour of lemons. It was 

 treated with pyrotartaric acid in absolute alcohol with /3-naphthy- 

 lamine, also dissolved in absolute alcohol (Doebner's reaction). 1 A 

 lemon-yellow crystalline substance was obtained on cooling, melt- 

 ing at 197 - 198° and is the alcyl-/3-naphtocinchoninic acid charac- 

 teristic of citral. The same aldehyde was also obtained when the 

 alcohol from the calcium chloride compound was oxidised. Citral 

 is therefore, the aldehyde obtained on oxidising the alcohol of the 

 ester in the oil of D. fascicular is. 



Determination of the acid. 

 The liquid obtained after saponification and separation of the 

 oil was made alkaline and evaporated nearly to dryness, this was 

 then acidified with sulphuric acid, the sulphate of potassium 

 separated and the liquid distilled. The volatile acid obtained in 

 the distillate was almost entirely acetic acid, although the odour 

 indicated the presence of a small quantity of another volatile acid. 

 The silver salt was obtained, purified, and the molecular value of 

 the acid determined. 0-2796 gram of the silver salt gave on 

 ignition 0-1789 gram silver = 63*98 per cent.; CH 3 COOAg requires 

 64*6 per cent, silver. The molecular value also shows 61*6 for 

 the acid instead of 60 acetic acid. The probable presence of a 

 small quantity of an acid with a higher molecular value is thus 

 indicated. The reactions were those of acetic acid, no formic acid 

 could be detected. The distillate was neutralised, evaporated 

 down and allowed to crystallise ; a good quantity of crystallised 

 acetate of sodium was obtained showing some well developed 

 monoclinic crystals. The principal acid of this ester is, therefore, 

 acetic acid. 



1 Ber. 27, 352. 



