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Question
Arrange the following.
In decreasing order of basic strength
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Solution
Aliphatic amines are more basic than aromatic amines. Therefore CH3CH2NH2 and CH3NH2 are more basic. Among the ethylamine and methylamine. ethylamine was experienced more +I effect than methylamine and hence ethylamine is more basic than methylamine.
Nitro group has a powerful electron-withdrawing group and they have both – R effect as well as – I effect. As a result, all the nitro anilines are weaker bases than aniline. In P-nitro aniline
both – R effect and – I effect of the NO2 group decrease the basicity. Therefore decreasing order of basic strength is,
Ethylamine > Methylamine > Aniline > p-nitro aniline
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