Some Molecules Are Able to Stabilize a Negative Charge by Passing

question 65

Multiple Choice

Some molecules are able to stabilize a negative charge by passing it from one atom to the next by a flip-flopping of double bonds. This occurs when the negative charge is one atom away from an oxygen double bond as follows. Note that the curved arrows indicate the movement of electrons: Why then is sulfuric acid so much stronger an acid than carbonic acid?

• A) In sulfuric acid, the negative charge is able to flip-flop to two additional oxygens rather than only one as is the case for carbonic acid.
• B) The two double bonded oxygens in tend to destabilize the single bonded oxygens once the hydrogen ions form, thus making sulfuric acid more acidic.
• C) Since carbonic acid has resonance stabilization and sulfuric acid does not, sulfuric acid is less stable and more acidic.
• D) The acid strength of two comparative molecules is directly proportional to the number of number of oxygens directly bonded to the central atom. Sulfuric acid, having four such oxygens, is more acidic.

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