Acid-Base Equilibria Man y factors contribute to the acidity of organic OH OH hy

Question

Acid-Base Equilibria Man y factors contribute to the acidity of organic OH OH 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, values. For each of the following pairs of compounds answer the following two multiple-choice questions OH NH OH H OH Questions .What factor(s) are the most important to consider 2. What is the relative trend in acidity and pK, of the when predicting the relative acidity of the two a. Electronegativity of the atom possessing the b. Resonance stabilization of the anionic conju two compounds? a. Structure I is the most acidic, and StructureI gate base. Inductive stabilization of the anionic conju- gate base. Hybridization of the atom possessing the b. Structure I is the most acidic, and Structure c. Structure II is the most acidic, and Structure II d. Structure II is the most acidic, and Structure II has the highest pK, has the lowest pK has the highest pK has the lowest pK C. d. e. The atomic size of the atom possessing the

Explanation / Answer

1. Ans : b, c( resonance stabilization of the anionic conjugate base for example phenol and benzyl alcohol, example c. Phenol is more acidic because phenoxide ion is resonance stabilized, benzyl oxy is not resonance stabilized)

Trifluoro acetic acid is more acidic than acetic acid because trifluoro acetate ion is stablized by inductive stabilization and acetic acid is not stabilized by inductive stabilization.

2. d (Thiophenol is more acidic than phenol because of resonance stabilization thiophenoxide ion than phenoxide ion).

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