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 is the strongest acid among the following? |
CH3COOH FCH2COOH F2CHCOOH F3CCOOH |
F3CCOOH |
The correct answer is option 4. F3CCOOH. To determine the strongest acid among the given compounds, we need to consider the effect of electron-withdrawing groups on the acidity of carboxylic acids. The presence of electronegative substituents like fluorine can significantly increase the acidity of a carboxylic acid by stabilizing the conjugate base through inductive effects. 1. CH₃COOH (Acetic Acid): Inductive Effect: The methyl group (CH₃) is slightly electron-donating due to hyperconjugation and inductive effects, which does not significantly increase acidity. Acidity: This is the baseline for comparison and is the weakest acid among the given options due to the lack of strong electron-withdrawing groups. 2. FCH₂COOH (Fluoroacetic Acid): Inductive Effect: The fluorine atom is highly electronegative and withdraws electron density through the sigma bond, stabilizing the conjugate base (fluoroacetate ion) and increasing the acidity of the acid. Acidity: More acidic than acetic acid due to the strong electron-withdrawing effect of one fluorine atom. 3. F₂CHCOOH (Difluoroacetic Acid): Inductive Effect: With two fluorine atoms attached, the electron-withdrawing effect is even stronger than in fluoroacetic acid, further stabilizing the conjugate base (difluoroacetate ion). Acidity: More acidic than fluoroacetic acid due to the additive electron-withdrawing effect of the two fluorine atoms. Inductive Effect: With three fluorine atoms, the electron-withdrawing effect is the strongest among the given compounds, providing maximum stabilization to the conjugate base (trifluoroacetate ion). Acidity: This is the strongest acid among the given options because the three fluorine atoms exert a very strong electron-withdrawing effect, significantly stabilizing the conjugate base. The order of acidity based on the inductive effects of the electron-withdrawing fluorine atoms is: \(\text{CH}_3\text{COOH} < \text{FCH}_2\text{COOH} < \text{F}_2\text{CHCOOH} < \text{F}_3\text{CCOOH}\) |