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Question

The correct increasing order of basic strength for the following compounds is


A

III < I < II

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B

III < II < I

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C

II < I < III

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D

II < III < I

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Solution

The correct option is C

II < I < III


The methyl group present in 4-methylaniline is an electron releasing group (via hyperconjugation). Hence, we could make a case for a greater-than-normal availability nitrogen lone pair to be donated. Hence, the third structure - 4-methylaniline is more basic than just plain aniline. In structure (II), the nitro group is strongly electron-withdrawing via conjugation and to a smaller extent even via (negative) inductive effect. Hence, in 4-nitroaniline, the availability of nitrogen's lone in the NH2 group is significantly diminished. Hence, (II) is less basic than (I), which is further less basic than (III). Hence the order of basic strength is (II) < (I) < (III)


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