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Which of the following is the weakest ac...

Which of the following is the weakest acid?

A

`p`-Chlorophenol

B

Phenol

C

`m`-Chlorophenol

D

`o`-Chlorophenol

Text Solution

Verified by Experts

The correct Answer is:
B


Although halogen is electron donating by resonance, its electron withdrawing inductive effect that decreases with increasing separation of `X` and `OH` predominates,making all the halophenols more acidic than phenol.The decreasing order of acid strength is

`pK_(a) = -log K_(a) =log 1//Ka`
Thus
lower `pK_(a) rarr` higher `K_(a) rarr` stronger acid
Notice that fluorophenols are relatively weaker acids than the corresponding chlorophenols. This is due to the fact that `+R_("effect")` of `F`(on account of smaller orbitals) is stronger than `+R("effect") of Cl`.
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