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Question
Arrange the following in increasing order of their basic strength:
C2H5NH2, C6H5NH2, NH3, C6H5CH2NH2 and (C2H5)2NH
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Solution
Considering the inductive effect of alkyl groups, NH3, C2H5NH2, and (C2H5)2NH can be arranged in the increasing order of their basic strengths as:
NH3 < C2H5NH2 < (C2H5)2NH
Again, C6H5NH2 has proton acceptability less than NH3. Thus, we have:
C6H5NH2 < NH3 < C2H5NH2 < (C2H5)2NH
Due to the −I effect of C6H5 group, the electron density on the N-atom in C6H5CH2NH2 is lower than that on the N-atom in C2H5NH2, but more than that in NH3. Therefore, the given compounds can be arranged in the order of their basic strengths as:
C6H5NH2 < NH3 < C6H5CH2NH2 < C2H5NH2 < (C2H5)2NH
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