The amino acid glycine (H2N–CH2–COOH) can participate in the following equilibria in water:
H2N–CH2–COOH + H2O ⇌ H2N–CH2–COO– + H3O+ Ka = 4.3 × 10-3
H2N–CH2–COOH + H2O⇌ +H3N–CH2–COOH + OH- Kb = 6.0 × 10-5
(a) Use the values of Ka and Kb to estimate the equilibrium constant for the intramolecular proton transfer to form a zwitterion: H2N–CH2–COOH ⇌ +H3N–CH2–COO–