Discussion
The order of basic strength of following amines is
(i) CH3NH2 (ii) (C2H5)2NH (iii)C6H5NH2 (iv)C6H5NHCH3
Answer: E
The order is (iii) < (iv) < (i) < (ii).
In the aryl amines the nitrogen lone pair is delocalised into the benzene ring, so aniline (iii) and N-methylaniline (iv) are much weaker bases than the alkyl amines. The extra methyl group on N makes N-methylaniline slightly more basic than aniline.
Among the alkyl amines, diethylamine (ii), a secondary amine with two electron-releasing ethyl groups, is more basic in water than methylamine (i). Options putting an aryl amine above an alkyl amine reverse the effect of resonance.
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