In HS-, I-, R-NH2, NH3 order of proton accepting tendency will be
- I- > NH3 > R-NH2 > HS-
- NH3 > R-NH2 > HS- > I-
- R-NH2 > NH3 > HS- > I-
- HS- > R-NH2 > NH3 > I-
Answer
(3) R-NH2 > NH3 > HS- > I-
Solution
Proton accepting tendency = Brønsted basic strength; a stronger base has a weaker conjugate acid.
R-NH2 vs NH3: the +I effect of the alkyl group increases electron density on N ⇒ R-NH2 > NH3.
NH3 vs HS-: conjugate acid NH4+ (pKa 9.3) is weaker than H2S (pKa 7) ⇒ NH3 > HS-.
I- is the conjugate base of the very strong acid HI ⇒ weakest base.
∴ R-NH2 > NH3 > HS- > I-
Answer: (3)