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Question

Arrange the following compounds in the order of decreasing acidity

  1. (i)>(ii)>(iii)>(iv)
  2. (iii)>(i)>(ii)>(iv)
  3. (iv)>(iii)>(i)>(ii)
  4. (ii)>(iv)>(i)>(iii)


Solution

The correct option is B (iii)>(i)>(ii)>(iv)
Electron withdrawing group increases the acidic strength and electron releasing group decreases the acidic strength.

NO2 has R effect and it is the strongest electron withdrawing group. So (iii) is the most acidic.
 Cl has both I and +R effect. But I predominates over +R. Therefore (i) is the second most acidic.
CH3 has hyperconjuagation effect and it is a weak acid than benzoic acid. Since it is in the ortho position and does not have ortho effect.
OCH3 has a +R effect which predominates over I effect. Hence (iv) is least acidic.

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