JEE AdvancedChemistryBasics of Organic ChemistryMCQ+1 / −0.25
Among the following compounds, the most acidic is
- Ap-nitrophenol
- Bp-hydroxybenzoic acid
- Co-hydroxybenzoic acid
- Dp-toluic acid
View written solutionFree
Correct answer: C
-
Identify the acidic functional groups
We compare the acidity of the given compounds:
- A: -nitrophenol
- B: -hydroxybenzoic acid
- C: -hydroxybenzoic acid
- D: -toluic acid
Phenols are generally less acidic than carboxylic acids.
Therefore, options B, C, D (carboxylic acids) are expected to be more acidic than A. -
Eliminate the weaker acid
- -nitrophenol has acidity enhanced by the electron-withdrawing group.
- But even substituted phenols usually have to .
- Carboxylic acids typically have to .
Hence, A is not the most acidic.
-
Compare the carboxylic acids: B, C, D
-
D: -toluic acid has a group at para position.
- is electron-donating by effect.
- It destabilizes the carboxylate ion slightly.
- So acidity decreases.
-
B: -hydroxybenzoic acid has an group at para position.
- The group has a weak effect but a strong effect.
- At para position, resonance donation dominates.
- This donates electron density to the ring and reduces acidity of the carboxylic acid compared to a strongly withdrawing substituent.
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C: -hydroxybenzoic acid is salicylic acid.
- It is known to be more acidic than benzoic acid and its para-hydroxy isomer.
- The key reason is the ortho effect.
- Also, the conjugate base is stabilized due to special interactions in the ortho position.
- In salicylic acid, intramolecular hydrogen bonding and ortho substitution favor greater acidity.
-
-
Use known acidity order
A standard order is: and also
Thus, among all given compounds, the most acidic is:
-
Option check
- A: No
- B: No
- C: Yes
- D: No
Therefore, the correct option is C.
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