Laboratory Methods of Organic Chemistry - Sciencemadness Dot Org

KEACTIONS OF NITEILBS 139
CH3.CN + 4H —> CH3.CH2.NH2.
Ethylamine
Other less important but general reactions may be indicated by the
following equations :
CH3.CN + H2S —> CH3.CS.NH2,
Thioacetamide
Jf.OH
CH3.CN + NH2.OH —>• CH3.
Oxime of acetamide
3 = CH3.CC =NR suggest another
constitution, namely, that of carbimide >C = NH with bivalent carbon.
The addition reactions of the nitriles (see above), which reactions are
also characteristic of hydrocyanic acid, can equally well be explained
on the basis of this second structural formula. In the nitrile form it
is at the triple bond between carbon and nitrogen that addition takes
place. In the " methylene form " this occurs at the two free valencies
of the bivalent carbon atom, e.g. :
,NHOH
>C=NH
+ H2NOH
\
*N]
HOHK
>C=NH
The hydrochloride of formiminoether is of practical importance. It
is produced in fine colourless crystals by passing dry hydrogen chloride
into a solution of equimolecular amounts of anhydrous hydrogen cyanide
and ethyl alcohol in absolute ether. The salt is slowly decomposed by
standing for a long time in the cold with alcohol, when ethyl orthoformate
and ammonium chloride are formed :
/OC2H5
/OC2H5
HC< + 2 HOCH2.CH3 = HCf-OC2H5 + NH4C1.
^NH.HCl \OC2H5