Chapter 4.6, Problem 1Q

Acid-Base Equilibria

Many factors contribute to the acidity of organic compounds. Electronegativity, resonance, induction, hybridization, aromaticity, and atomic size, all play a role. In the following comparisons, you are asked to identify the factor(s) that would be most important to analyze when predicting relative acidity, and then to predict the trend in acidity and pK_a values. For each of the following pairs of compounds answer the following two multiple-choice questions.

1. 1. What factor(s) are the most important to consider when predicting the relative acidity of the two compounds?
   1. a. Electronegativity of the atom possessing the hydrogen.
   2. b. Resonance stabilization of the anionic conjugate base.
   3. c. Inductive stabilization of the anionic conjugate base.
   4. d. Hybridization of the atom possessing the hydrogen.
   5. e. The atomic size of the atom possessing the hydrogen.