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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 isAmong the following compounds, the most acidic is

Options

  1. Ap-nitrophenol
  2. Bp-hydroxybenzoic acid
  3. Co-hydroxybenzoic acid
  4. 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 - OH\mathrm{OH} 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 H\mathrm{H}-bond which outweight the electron donating resonance effect of −OH-\mathrm{OH}. Among the following compounds, the most acidic is
The overall order of acid-strength of given four acids is ortho-hydro xyx y benzoic acid \left(p K_a=298\right)>ToluicacidpKa=4.37)>pToluic acid \left.p K_a=4.37\right)>p-hydroxybenzoic acid \left(p K_a=4.58\right)> p−nitrophenol(pKa=7.15)-nitrophenol \left(p K_a=7.15\right).
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