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Amines

Question
CBSEENCH12009151

Arrange the following in the order of decreasing basicity:
C6H3NH2, p-NO2C6H4NH2, m-NO2.C6H4NH2, p-CH3 OC6H4NH2.

Solution

p-CH3OC6H4NH2 > C6H5NH2 > m-NO2.C6H4. NH2 > p-NO2.C6H4.NH2-NO2 group in m-position weakens the base due to inductive effect while in o- and p- positions it weakens the base due to -I effect and extended straight pi bonding.