Orgo I: Would water be a suitable proton source to protonate the following compound? (Please show a drawing(s) of how you got your answer. I'm confused how to draw the reactions/the associated arrows)

I have the solution from the solutions manual, but there is no drawing, and I'm getting an incorrect answer. Please draw the reactions/transfer/arrows so I can see how to come up with the correct answer. The solution manual states "No, water would not be a suitable proton source in this case. This anion is the conjugate base of a carboxylic acid. The negative charge is resonance stabilized and is more stable than hydroxide."

  • A picture of the problem (3.42) was added, I'm not sure why it wasn't added to the description. Sorry about that Ann commented about 3 years ago