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Question

Arrange the following
(i) In decreasing order of the pKb values: C2H5NH2,C6H5NHCH3,(C2H5)2NH and C6H5NH2
(ii) In increasing order of basic strength: C6H5NH2,C6H5N(CH3)2,(C2H5)2NH and CH3NH2
(iii) In increasing order of basic strength:
(a) Aniline, p-nitroaniline and p-toluidine

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Solution

(i) Stronger base has lower pKb value.
C6H5NH2>C6H5NHCH3>C2H5NH2>(C2H5)2NH
(ii) Increasing order of basicity is as follows:
C6H5NH2<C6H5NHCH3<CH3NH2<(C2H5)2NH
(iii) Increasing order of basic strength.
(a) p-nitroaniline < aniline < p-toluidine
(b) PhNH2<PhNHCH3<PhCH2NH2
(iv) In decreasing order of basic strength in gas phase:
Et3N>Et2NH>EtNH2>NH3
The stabilization of conjugate acids due to hydrogen bonding is absent.
(v) Increasing order of boiling point
Me2NH<EtNH2<EtOH
(vi) Increasing order of solubility in water:
PhNH2<Et2NH<EtNH2

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