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Chapter 17: Q17-59E (page 567)

Rank the following substituted phenol in the increasing order of acidity, and explain your answer:

Short Answer

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The answer is

Step by step solution

01

Acidity in phenols

The acidity of alcohols can be defined as the tendency of alcohols to donate the protons and forms a stable oxide anion. The acidity of alcohols depends on the stability of the oxide anion formed.

02

Explanation

The increasing order of acidity is shown below.

Electron-withdrawing groups on phenol can stabilise the anions formed after losing the protons(that is phenoxide ion) and hence become more acidic. The electron-donating groups, in turn, decrease acidity.

-CN group can stabilise the phenoxide ion by mesomeric effect.

-F is an electronegative atom.

-OCH3is an electron donating group that will decrease the acidity of the phenol.

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