Consider the following acid-base reactions: a. Use curved arrows to show each a...

Consider the following acid-base reactions:

a. Use curved arrows to show each acid base reaction.

b. Based on the pKa data, which alcohol is a stronger acid?

c. Which conjugate base is lower in potential energy (a weaker base)?

Warning!! Common Sticking Point!! Many students think that conjugate base B should be lower in potential energy because A has an unfavorable negative carbon associated with it. An additional resonance structure (even if it is not very favorable) can only “help” lower the potential energy of a species. It cannot hurt. The following analogy helps illustrate this point.

Consider two teams of postal workers racing to postmark 1000 envelopes. Team A consists of a fast worker and a slow worker. Team B consists of a single fast worker. Assume the two fast workers work at the same pace, and the slow worker doesn’t bother his fast teammate.

This means Team A will postmark 1000 envelopes before Team B since the slow worker helps some and doesn’t hurt at all.

d. Explain how this story relates to the example at the top of the page.