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  4. Which one of the following compounds has the most acidic nature?

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Q. Which one of the following compounds has the most acidic nature?

AIPMTAIPMT 2010Alcohols Phenols and Ethers

Solution:

Presence of electron withdrawing substituent increases the acidity while electron releasing substituent, when present, decreases the acidity.
Phenyl is an electron withdrawing substituent while $- CH_3$ is an electron releasing substituent.
Moreover, phenoxide ion is more resonance stabilised as compared to benzyloxide ion, thus releases proton more easily. That's why phenol is a strong acid among the given compounds