[sharbeldam]

As much as I love organic chemistry, I dont think it loves me back (Flashback to every girl I've loved) because it always seem to put me in a difficult position with my students that i tutor and I just stare at the question without an answer.

If I'm comparing the acidity of ortho nitrophenol with para nitrophenol, I know that para is more acidic because it has resonance+I effect (ortho too) but ortho-nitrophenol has hydrogen bonding that reduces its acidity and hence ortho is less acidic -> that means that in this case Hydrogen bonding effect> I effect (Since NO2 is closer and withdraws electron more and should stabilize the conjugate base more.)


If I compare ortho flurophenol with para-fluorophenol, same logic but ortho is more acidic because I effect here is stronger than the hydrogen bonding effect.

Is there a rule to know when hydrogen bonding effect is stronger effect than I effect? if the atom is very electronegative like F, the I effect should be stronger, but so does the hydrogen bonding...

I really appreciate the *delete me* thanks.

[rolnor]

Is there hydrogenbonding in o-fluorophenol? I think not.

[sharbeldam]

Why not? The hydrogen that is connected to phenol oxygen with electron pair on F?

[AWK]

In crystals, 2-fluorophenol forms hydrogen bonds only between phenolic groups.

[sharbeldam]

This is not true then? Why?

[AWK]

https://onlinelibrary.wiley.com/doi/10.1002/chem.19970030115

[sharbeldam]

Everything I have been taught in the past apparently has been a lie.

Appreciate the help.

[AWK]

Fluoride anion forms very strong hydrogen bonds