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Question

Arrange the following in the increasing order of acidity.

A
Phenol
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B
Methanol
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C
4-Nitrophenol
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D
Isopropanol
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E
Tert-butanol
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Solution

Acidity of aliphatic alcohols is in the order: primary>secondary>tertiary. This is because, the electron donating alkyl groups on carbon, attached to the -OH group increases the electron density on oxygen atom and hence reduces the polarity of O-H bond. This decreases the acid strength of secondary and tertiary alcohols.
Obviously, nitrophenols are more acidic than phenols due to the electron withdrawing nitro group.

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