In the following compound two protons are clearly identified. Determine which of the two is more acidic. After comparing the conjugate bases, you should get stuck on the following question: Is it more stabilizing for a negative charge to be spread out over one oxygen atom and three carbon atoms or to be spread out over two oxygen atoms? Draw all of the resonance structures of each conjugate base, and then take a look at the pK_avalues listed in the following table.

Transcribed Image Text:

ACID рк, CONJUGATE BASE Strongest acid Weakest base H-O-S-O-H -9 н-о- CI-H -7 н -2.9 н н - 1.74 4.75 9.0 нн "н 9.9 15.7 16 18 н 19.2 нн нн 25 Н-сс-н н- Н 38 н н н н н н н Н 44 Н Н Weakest Strongest н н н acld base Н-С—с- Н-с—с—н 50 н Н н I. Н