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Which of the following has maximum acidi...

Which of the following has maximum acidic strength ?

A

o-Nitrobenzoic acid

B

m-Nitrobenzoic acid

C

p-Nitrobenzoic acid

D

p-Nitrophenol.

Text Solution

AI Generated Solution

The correct Answer is:
To determine which of the given compounds has the maximum acidic strength, we need to analyze the structures and the effects of substituents on the acidity of benzoic acid derivatives. Here’s a step-by-step solution: ### Step 1: Identify the Compounds The compounds in question are: 1. Ortho-nitrobenzoic acid 2. Meta-nitrobenzoic acid 3. Para-nitrobenzoic acid 4. p-Nitrophenol ### Step 2: Understand the Role of the Nitro Group The nitro group (NO2) is an electron-withdrawing group. Its presence on the benzene ring affects the acidity of the carboxylic acid group (COOH) by stabilizing the negative charge on the conjugate base (the carboxylate ion, COO⁻) after deprotonation. ### Step 3: Analyze the Position of the Nitro Group - **Ortho-nitrobenzoic acid**: The nitro group is positioned adjacent to the carboxylic acid group. This proximity allows for strong resonance and inductive effects, stabilizing the conjugate base. - **Meta-nitrobenzoic acid**: The nitro group is positioned one carbon away from the carboxylic acid group. The electron-withdrawing effect is weaker here compared to the ortho and para positions. - **Para-nitrobenzoic acid**: The nitro group is opposite the carboxylic acid group. It can still exert a strong electron-withdrawing effect, stabilizing the conjugate base. - **p-Nitrophenol**: This compound has a hydroxyl (OH) group, which can also influence acidity, but the presence of the nitro group will still play a significant role. ### Step 4: Compare the Acidity - The acidity is generally enhanced when the electron-withdrawing group is in the ortho or para position due to the resonance stabilization of the conjugate base. - The ortho position provides the strongest stabilization due to both resonance and inductive effects. - The para position also provides stabilization but is slightly less effective than the ortho position. - The meta position is the least effective in enhancing acidity. ### Conclusion Based on the analysis, **ortho-nitrobenzoic acid** has the maximum acidic strength due to the strong electron-withdrawing effect of the nitro group in the ortho position, which stabilizes the conjugate base effectively. ### Answer **Ortho-nitrobenzoic acid (Option 1) has the maximum acidic strength.** ---

To determine which of the given compounds has the maximum acidic strength, we need to analyze the structures and the effects of substituents on the acidity of benzoic acid derivatives. Here’s a step-by-step solution: ### Step 1: Identify the Compounds The compounds in question are: 1. Ortho-nitrobenzoic acid 2. Meta-nitrobenzoic acid 3. Para-nitrobenzoic acid 4. p-Nitrophenol ...
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