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Arrange the following in decreasing order of basicity: (I) aniline, (II) N,N-dimethylaniline, (III) p-nitroaniline, (IV) m-nitroaniline.

1. I > II > III > IV
2. IV > III > II > I
3. II > I > IV > III
4. I > IV > III > II

Correct answer: II > I > IV > III

Solution

N,N-dimethylaniline is most basic due to +I effect of methyls. Aniline is next. Among nitroanilines, meta-nitro withdraws by induction only while para-nitro also withdraws by resonance (lone pair of N is directly delocalised onto the nitro group), making p-nitroaniline least basic.

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