Practicing Success
Both alcohols and phenols contain a hydroxyl group, but phenols are more acidic than alcohols. Whereas the acid strength of aliphatic alcohols mainly depends upon the inductive effects, and acid strength of phenols depends upon a combination of both inductive and resonance effects of the substituent and its position on the benzene ring. |
Which of the following is the strongest acid?
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FCH2COOH ClCH2COOH BrCH2COOH ICH2COOH |
FCH2COOH |
The correct answer is option 1. \(FCH_2COOH\). To determine the strongest acid among the given compounds, we need to consider the electron-withdrawing inductive effects of the halogen substituents. The stronger the electron-withdrawing effect, the more the conjugate base is stabilized, resulting in a stronger acid. 1. \(FCH_2COOH\) (Fluoroacetic Acid): Inductive Effect: Fluorine is the most electronegative halogen, thus it has the strongest electron-withdrawing inductive effect. This significantly stabilizes the conjugate base (fluoroacetate ion). Acidity: High, due to the strong electron-withdrawing effect of fluorine. 2. \(ClCH_2COOH\) (Chloroacetic Acid): Inductive Effect: Chlorine is less electronegative than fluorine but still highly electronegative. It provides a strong electron-withdrawing inductive effect, though weaker than that of fluorine. Acidity: High, but less than fluoroacetic acid. 3. \(BrCH_2COOH\) (Bromoacetic Acid): Inductive Effect: Bromine is less electronegative than chlorine, resulting in a weaker electron-withdrawing inductive effect. Acidity: Moderate, less than chloroacetic acid. 4. \(ICH_2COOH\) (Iodoacetic Acid): Inductive Effect: Iodine is the least electronegative among the halogens listed, resulting in the weakest electron-withdrawing inductive effect. Acidity: Lowest among the given compounds. The order of acidity based on the inductive effects of the halogen substituents is: Thus, the strongest acid among the given compounds is \(FCH_2COOH\) (fluoroacetic acid). |