Arrange the following:
In increasing order of basic strength: C6H5NH2, C6H5NHCH3, C6H5CH2NH2.
C6H5NHCH3 is more basic than C6H5NH2 due to the presence of electron-donating −CH3 group in C6H5NHCH3.
Again, in C6H5NHCH3, −C6H5 group is directly attached to the N-atom. However, it is not so in C6H5CH2NH2. Thus, in C6H5NHCH3, the −R effect of −C6H5 group decreases the electron density over the N-atom. Therefore, C6H5CH2NH2 is more basic than C6H5NHCH3.
Hence, the increasing order of the basic strengths of the given compounds is as follows:
C6H5NH2 < C6H5NHCH3 < C6H5CH2NH2.
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