The correct order of basic nature in aqueous solution for the bases NH3, H2N-NH2, CH3CH2NH2, (CH3CH2)2NH and (CH3CH2)3N is :
- NH3 < H2N-NH2 < (CH3CH2)3N < CH3CH2NH2 < (CH3CH2)2NH
- H2N-NH2 < NH3 < (CH3CH2)3N < CH3CH2NH2 < (CH3CH2)2NH
- H2N-NH2 < NH3 < CH3CH2NH2 < (CH3CH2)3N < (CH3CH2)2NH
- NH3 < H2N-NH2 < CH3CH2NH2 < (CH3CH2)2NH < (CH3CH2)3N
Answer
(3) H2N-NH2 < NH3 < CH3CH2NH2 < (CH3CH2)3N < (CH3CH2)2NH
Solution
Hydrazine: the –I effect of the neighbouring -NH2 group lowers the electron density on N weaker base than NH3 (pKb 5.9 vs 4.75).
Ethylamines are stronger bases than NH3 because of the +I effect of ethyl groups.
In aqueous solution, +I effect, H-bonding (solvation) of the cation and steric hindrance together decide the order. As per NCERT, for ethyl groups: (C2H5)2NH > (C2H5)3N > C2H5NH2 > NH3
(pKb: 3.00, 3.25, 3.29, 4.75)
H2N-NH2 < NH3 < CH3CH2NH2 < (CH3CH2)3N < (CH3CH2)2NH
Answer: (3)