Which of the following represents the correct order of the acidity in the given compounds ?
- FCH2COOH > CH3COOH > BrCH2COOH > ClCH2COOH
- BrCH2COOH > ClCH2COOH > FCH2COOH > CH3COOH
- FCH2COOH > ClCH2COOH > BrCH2COOH > CH3COOH
- CH3COOH > BrCH2COOH > ClCH2COOH > FCH2COOH
Answer
(3) FCH2COOH > ClCH2COOH > BrCH2COOH > CH3COOH
Solution
As per NCERT, electron-withdrawing groups increase the acidity of carboxylic acids by stabilising the carboxylate ion through –I effect.
−I effect: F > Cl > Br (order of electronegativity); acetic acid has no halogen and its CH3 group shows +I effect, so it is the weakest.
⇒ FCH2COOH (pKa 2.66) > ClCH2COOH (2.86) > BrCH2COOH (2.90) > CH3COOH (4.76)
Answer: (3)