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?


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