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NEET 2010
Exam
NEET
Year
2010
Subject
Chemistry
Chapter
General Organic Chemistry

NEET 2010 · Chemistry · General Organic Chemistry

Among the following four compounds A. Phenol B. Methyl phenol C....

Among the following four compounds A. Phenol B. Methyl phenol C. meta-nitrophenol D. para nitrophenol the acidity order is

Options

  1. AD >> C >> A >> B
  2. BC >> D >> A >> B
  3. CA >> D >> C >> B
  4. DB >> A >> C >> D

Correct answer

A. D >> C >> A >> B

Step-by-step solution

An electron withdrawing group (-I showing group like −NO2,−CN)\left.-\mathrm{NO}_2,-\mathrm{CN}\right) stabilises the phenoxide ion, thus when present, increases the acidity of phenol. On the other hand electron releasing groups (+I+I showing group like −CH3,−C2H5-\mathrm{CH}_3,-\mathrm{C}_2 \mathrm{H}_5), when present, decrease the acidity of phenol by destabilising phenoxide ion. Hence, the correct order of acidity of given compounds is (\underset{(D)}{\text{p-nitrophenol}} > \underset{(C)}{\text{m-nitrophenol}} > \underset{(A)}{\text{phenol}} > \underset{(B)}{\text{methyl phenol}}) (due to intermolecular H -bonding)
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