(a) Ion A is more acidic than ion B in the gas phase. Is this the acidity order predicted by hybridization arguments? Explain.

(b) Ion B is less acidic because it is stabilized by resonance, whereas ion A is not. Show the resonance structure for ion B, and, with the aid of an energy diagram, show why stabilization of ion B should reduce its acidity.

(c) In aqueous solution, ion A is less acidic than ion B. Explain.

Transcribed Image Text:

+ H₂C-OH₂ H3C-CH-OH A B +