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Question
Arrange the following in increasing order of their basic strength:
C2H5NH2, (C2H5)2NH, (C2H5)3N, C6H5NH2
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Solution
Considering the inductive effect and the steric hindrance of the alkyl groups, C2H5NH2, (C2 H5)2NH2,and their basic strengths as follows:
C2H5NH2 < (C2H5)3N < (C2H5)2NH
Again, due to the −R effect of C6H5 group, the electron density on the N atom in C6H5NH2 is lower than that on the N atom in C2H5NH2.
Therefore, the basicity of C6H5NH2 is lower than that of C2H5NH2. Hence, the given compounds can be arranged in the increasing order of their basic strengths as follows:
C6H5NH2 < C2H5NH2 < (C2H5)3N < (C2H5)2NH
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