[cookiecrumbzz]

How is   less activated than ? Doesn't the CH3 group in -OCH3 push more electron density into the benzene ring by its +I effect?

[kriggy]

Because when the alkoxy group donates the electrons there is positive charge on the oxygen which is unfavorable due to its high electronegativity however    the phenolic hydrogen is acidic so when it disociates, there will be neative charge on the oxygen which makes the activation stronger.

[cookiecrumbzz]

Because when the alkoxy group donates the electrons there is positive charge on the oxygen which is unfavorable due to its high electronegativity however    the phenolic hydrogen is acidic so when it disociates, there will be neative charge on the oxygen which makes the activation stronger.

 You're talking about the phenoxide ion. But if we draw resonance structures for phenol, we get a positive charge on O as well.
 Are you saying that phenol will spontaneously dissociate into phenoxide ion and H⁺ so that it no longer has the positive charge on O?

[kriggy]

Basicaly yes. I dont think it will spontaneusly disociate its pKa is ~9 but if you draw the resonance for phenol and you have positive charge on oxygen, then the proton can disociate and you no longer has positive oxygen

[cookiecrumbzz]

 Okay, that's convincing. Thanks for answering!