JEE Advanced 2011Paper 1
- Exam
- JEE Advanced
- Year
- 2011
- Paper
- Paper 1
- Subject
- Chemistry
- Chapter
- General Organic Chemistry
JEE Advanced 2011 · Paper 1 · Chemistry · General Organic Chemistry
Among the following compounds, the most acidic is
Among the following compounds, the most acidic is
Options
- Ap-nitrophenol
- Bp-hydroxybenzoic acid
- Co-hydroxybenzoic acid
- Dp-toluic acid
Correct answer
C. o-hydroxybenzoic acid
Step-by-step solution
A monosubstituted benzoic acid is stronger than a monosubstituted phenol as former being a carboxylic acid. Among the given substituted benzoic acid, ortho-hydroxy acid is strongest acid although - cause electron donation by resonance effect which tends to decrease acid strength. It is due to a very high stabilization of conjugate base by intramolecular -bond which outweight the electron donating resonance effect of .

The overall order of acid-strength of given four acids is ortho-hydro benzoic acid \left(p K_a=298\right)>-hydroxybenzoic acid \left(p K_a=4.58\right)> p.
The overall order of acid-strength of given four acids is ortho-hydro benzoic acid \left(p K_a=298\right)>-hydroxybenzoic acid \left(p K_a=4.58\right)> p.