Which compound would be the strongest acid?
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

E) 2,2-dichlorobutanoic acid would be the strongest acid because the electron-withdrawing inductive effect of the chlorine atoms stabilizes the carboxylate anion formed after deprotonation. The closer these substituents are to the carboxylic acid group, the stronger the inductive effect, making the acid stronger. In this case, having both chlorine atoms at the 2 position maximizes this effect.

Which Compound Would Be the Strongest Acid