Which one of the given compounds is a stronger acid and why?
CH2FCH2CH2COOH оr CH3CHFCH2COOH
Ans.
To determine which compound is a stronger acid between CH2FCH2CH2COOH and CH3CHFCH2COOH, we need to consider the stability of the conjugate base formed after the acid loses a proton.
Let’s examine the conjugate bases:
CH2FCH2CH2COOH will form the conjugate base CH2FCH2CH2COO^-, which is stabilized by resonance with the adjacent carbonyl group. This resonance delocalizes the negative charge on the oxygen atom, stabilizing the conjugate base.
CH3CHFCH2COOH will form the conjugate base CH3CHFCH2COO^-, which does not have the possibility of resonance stabilization.
Resonance stabilization of the conjugate base increases its stability, making the corresponding acid stronger. Therefore, CH2FCH2CH2COOH is the stronger acid compared to CH3CHFCH2COOH due to the resonance stabilization of its conjugate base.