Distinguishing between primary, secondary and tertiary amines

Distinguishing between primary, secondary and tertiary amines

Distinguishing between primary, secondary and tertiary amines

Reagent: nitrous acid (NaNO2, HCl (0-50C))

Observation

(i) Primary amine: effervescence

Equation

RNH2 + NaNO2 + 2HCl     →           RCl  +  N2(g) +H2O + NaCl

(ii) Secondary amines: yellow oil liquid

Equation

R2NH  + NaNO2  +  HCl    →           R2N-NO  + NaCl  +  H2O

(iii) Tertiary amines: no observable change du to the formation of soluble diazonium salts

Equation

R3N  +  NaNO2  +  4HCl    →           RN2Cl  +  2RCl   +  NaCl  +  2H2O

(iv) Aromatic amine: no observable change due to the formation of soluble diazonium salts

Equation

ArNH2  +  NaNO2  + 2HCl →          ArN2Cl  +   NaCl  +  2H2O

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