Which of the following substituted phenol is most acidic in nature?
(I) (II)
(III) (IV)

Question

Which of the following substituted phenol is most acidic in nature? (I) (II) (III) (IV)

TestHub · Accepted Answer

Fluorine stabilises the phenoxide anion by its -I effect. One fluorine stabilises more than none, two more than one, and three more than two, with the ortho and para positions also helping through the ring. Compound (IV) carries fluorines at 2, 4 and 6, so its conjugate base is the most stabilised and (IV) is the most acidic.

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