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What is the hybridization of oxygen in phenol molecule? I assume it is $sp^3$ hybridized because it forms 2 bonds - 1 with benzene, another with hydrogen, as in how oxygen is hybridized in a water molecule - $sp^3$. Now the problem is, my A - level lecturers insist that it is the p orbital of oxygen that overlaps with the delocalised electrons of benzene ring, not $sp^3$. This means that oxygen can either be unhybridized, $sp$, or $sp^2$ hybridized. So which is true?

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    $\begingroup$ Water is not $sp^3$ hybridized (see the first part of this answer). I imagine phenol is the same, with the p-type lone pair engaged in resonance with the ring. $\endgroup$ – bon Jul 18 '15 at 10:13
  • $\begingroup$ Referring to the link you've provided, the oxygen atom would be sp2 hybridized if it is bonded to another atom which is also sp2 hybridized, but this is not the case for water. If water is not sp3 hybridized then it would'nt have its 'bent' shape. Going back to the main point, I recall that when the orbital of oxygen overlaps with benzene ring, it will get a partial double bond, so can I assume that there exists such a resonant structure where there is a double bond between C and O? If that is legit, then the sp2 model should be correct. $\endgroup$ – Jye Quan Jul 19 '15 at 15:05
  • $\begingroup$ Of course there are such structures, but it's not that simple. $\endgroup$ – Mithoron Jul 19 '15 at 16:31