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Question
Arrange the following:
In increasing order of basic strength:
C6H5NH2, C6H5N(CH3)2, (C2H5)2NH and CH3NH2
Solution
C6H5N(CH3)2 is more basic than C6H5NH2 due to the presence of the +I effect of two −CH3 groups in C6H5N(CH3)2. Further, CH3NH2 contains one −CH3 group while (C2H5)2NH contains two −C2H5groups. Thus, (C2H5)2NH is more basic than C2H5NH2.
Now, C6H5N(CH3)2 is less basic than CH3NH2 because of the −R effect of −C6H5 group.
Hence, the increasing order of the basic strengths of the given compounds is as follows:
C6H5NH2 < C6H5N(CH3)2 < CH3NH2 < (C2H5)2NH
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