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In acidic medium aniline is m-directing because of protonation of $\ce{NH2}$ group. But why doesn't the same happen in case of phenol, why is phenol an extremely weaker base as compared to aniline?

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marked as duplicate by Mithoron, Waylander, Tyberius, Todd Minehardt, ashu Apr 16 at 13:11

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    $\begingroup$ Because it does not protonate so the electrons from the O are available to the ring. $\endgroup$ – Waylander Apr 14 at 16:48
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    $\begingroup$ Phenol is much weaker base, compared to aniline. $\endgroup$ – Poutnik Apr 14 at 17:32
  • $\begingroup$ I've seen that but cannot find a satisfactory explanation, it also doesn't address the question as to why phenol is not protonated at all. $\endgroup$ – Sanom Dane Apr 14 at 19:22
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    $\begingroup$ Why is water a weaker base than ammonia? Same thing here. $\endgroup$ – Ivan Neretin Apr 15 at 8:39
  • $\begingroup$ So is basicity of phenol comparable to that of water? $\endgroup$ – Sanom Dane Apr 15 at 8:55