MALONIC ACID. 157 



mass, easily soluble in water, alcohol, and ether. Com- 

 bines with the bisulphites of the alkalies ; with am- 

 monia, water being eliminated, forming bases free of 

 oxygen ; glycosine C 6 H 6 E" 4 and glyoxaline&TPN 2 . Very 

 dilute nitric acid oxidizes it, forming glyoxylic acid ; 

 concentrated nitric acid converts it into oxalic acid. 



CH 2 .OH 

 Glycolacetal, 252 Is P roduce(i b J tlie 



action of alcoholic potassa on bromacetal (p. 105). 

 Colorless liquid of a pleasant odor, boiling without 

 decomposition at 167. 



CH.(O.C 2 H 5 ) 2 

 Glyoxalacetal, ^ ,Q Q 2 jj 5 \ 2 I s obtained by al- 



lowing sodium alcoholate to act upon dichloracetal. 

 Colorless liquid, boiling at 180. 



CHO 

 Glyoxylic acid, C 2 H 2 3 = Is produced by 



heating dibromacetic acid with water and silver oxide ; 

 by heating ethyl dichloracetate with water to 120 ; 

 and, together with glycolic acid, by slow oxidation of 

 ethyl alcohol with nitric acid. Tenacious, pale-yellow 

 syrup; easily soluble in water; volatile with water 

 vapor without undergoing decomposition. Unites with 

 nascent hydrogen, forming glycolic acid. Its salts, 

 with the alkalies, combine with the bisulphites of the 

 alkalies, forming crystallizing compounds. 



The calcium salt (C 2 H0 3 ) 2 Ca + 2H 2 crystallizes in 

 hard prisms, which are difficultly soluble. In its solu- 

 tion, lime-water gives a white precipitate, soluble in 

 acetic acid. By boiling with lime-water, it is decom- 

 posed, yielding calcium glycolate and oxalate. 



2. Malonic Acid. 



Formation. By careful oxidation of malic acid with 

 potassium bichromate ; by heating cyanacetic acid (p. 

 14 



