Which compound would be expected to have the highest pK_a? A)4,4-dichlorobutanoic acid B)3,4-dichlorobutanoic acid C)3,3-dichlorobutanoic acid D)2,3-dichlorobutanoic acid E)2,2-dichlorobutanoic acid

Question

Quizplus · Accepted Answer

The pKa of a carboxylic acid is influenced by the electron-withdrawing effects of substituents. Chlorine is an electron-withdrawing group, and its effect is stronger when it is closer to the carboxyl group. In 4,4-dichlorobutanoic acid, the chlorine atoms are farthest from the carboxyl group, resulting in the least electron-withdrawing effect and thus the highest pKa among the given options.

Which Compound Would Be Expected to Have the Highest PKa

Which Compound Would Be Expected to Have the Highest PK_a