Organic Chemistry Basics 2 Question 84
84. Arrange the following in the order of their increasing basicity. $p$-toluidine, $\mathrm{N}, \mathrm{N}$-dimethyl- $p$-toluidine, $p$-nitroaniline, aniline.
$(1985,1 \mathrm{M})$
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Solution:
- $p$-nitroaniline $<$ aniline $<p$-toluidine $<\mathrm{N}$,N-dimethyl- $p$-toluidine. Nitro group, by electron withdrawing resonance effect decreases the basic strength. Methyl group by electron donating inductive effect, increases basic strength.
