(a) How will you distinguish between the following pairs of compounds :
(i) Aniline and Ethanamine
(ii) Aniline and N-methylaniline
(b) Arrange the following compounds in decreasing order of their boiling points :
Butanol, Butanamine, Butane
a) (i) Aniline and Ethanamine can be distinguished by Adding Ice cold (NaNO2 + HCl) followed by phenol or β-Naphthol to both the compounds. Aniline forms orange red dye while ethylamine doesn’t.
ii) Aniline and N-methylaniline can be distinguished by Adding CHCl3 and KOH (alc.) to both the compounds. Aniline gives foul smelling isocyanide while N-Methylaniline doesn’t.
b) Butanol > Butanmine > Butane