ia6 Biological Chemistry. 



The tertiary compound, on treatment with an alkyl iodide, 

 will yield the " quaternary " base 



(C 2 H 5 ) 3 N + C,H 8 I m N(C 2 H 5 ) 4 I (3) 



Even in these reactions, when the theoretical amounts 

 of the various reagents are employed, the pure bases are 

 not obtained, for the diethylamine obtained according to 

 equation (1) will partly undergo the reactions of equation 

 (2), and the trimethylamine will undergo the reaction 

 indicated in equation (3). 



If the mixture obtained in these reactions is distilled 

 with steam, the secondary and tertiary amines will distil 

 over and leave the quaternary compound behind. If the 

 residue is then neutralized with hydrochloric acid and 

 evaporated to dry ness, the quaternary ammonium chloride 

 thus obtained can be separated from the potassium salt by 

 extraction with alcohol. The secondary and tertiary 

 alcohols can be separated by treatment with nitrous acid 

 by a method to be described below. 



Primary Amines. These substances, of the type 

 NH 2 K, can be obtained, in addition to the method above 

 described, by the following reactions : (a) When an acid 

 amide is treated with bromine and potassium hydroxide 

 it yields an amine with one carbon atom less. The re- 

 action is a somewhat complex one, but the final result can 

 be represented by the following equations (in the case of 

 acetamide) 



CH 3 CO NH 2 + Br 2 + KOH = CH 3 CO NHBr + KBr + H 2 



CH 3 .CO-NHBr + 3KOH = CH 3 -NH 2 + KBr + K 2 C0 8 + H 2 



To prepare ethylamine, propionamide (the amide of pro- 

 pionic acid), which has one carbon atom more, is submitted to 

 the same reaction. (6) Primary amines can also be obtained 

 by the treatment of the nitriles with nascent hydrogen 



