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Q. Consider the following compounds

$1.$ Phenol

$2.$ o-chlorophenol

$3.$ m-chlorophenol

$4.$ p-chlorophenol

Place these compounds in the decreasing order of acidity

NTA AbhyasNTA Abhyas 2020

Solution:

Although Cl is electron donating by resonance, yet its electron withdrawing acid-strengthening inductive effect (that decreases with increasing separation of Cl and OH) predominates over electron donating, acid weakening resonance effect. This makes all chlorophenols more acidic than phenol. As -I effect decreases with distance so the decreasing order of acidity is 2 > 3 > 4 > 1.