Answer:
CH₃CH₂CH₂COOH > CH₃CH₂COOH > ClCH₂CH₂COOH > ClCH₂COOH
Explanation:
Electron-withdrawing groups (EWGs) increase acidity by inductive removal of electrons from the carboxyl group.
Electron-donating groups (EDGs) decrease acidity by inductive donation of electrons to the carboxyl group.
- The closer the substituent is to the carboxyl group, the greater is its effect.
- The more substituents, the greater the effect.
- The effect tails off rapidly and is almost zero after about three C-C bonds.
CH₃CH₂-CH₂COOH — EDG — weakest — pKₐ = 4.82
CH₃-CH₂COOH — reference — pKₐ = 4.75
ClCH₂-CH₂COOH — EWG on β-carbon— stronger — pKₐ = 4.00
ClCH₂COOH — EWG on α-carbon — strongest — pKₐ = 2.87
