To answer this question we must know Kb of CH3CH2NH2 is 5.6x10⁻⁴, and for C6H5NH2 is 4.0x10⁻¹⁰. And the CH3CH2NH3+ and C6H5NH3+ are related with these substances because are their conjugate base. That means:
pKa of CH3CH2NH3+ = CH3CH2NH2; C6H5NH3+ = C6H5NH2
Also, Kw / Kb = Ka
Thus:
pKa of CH3CH2NH3+/CH3CH2NH2 is:
Kw / kb = Ka = 1.79x10⁻¹¹
-log Ka = pKa
pKa = 10.75
pKa of C6H5NH3+/ C6H5NH2 is:
Kw / kb = Ka = 2.5x10⁻⁵
-log Ka = pKa
pKa = 4.6
That means CH3CH2NH3+/CH3CH2NH2 would have the largest pKa
