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Topic: Hydroxyacetophenone more acidic than phenol?  (Read 4894 times)

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Offline zephen53

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Hydroxyacetophenone more acidic than phenol?
« on: December 14, 2008, 10:41:17 AM »
i'm just a bit confused about whether the C=O group withdraws or donates electrons to the benzene ring ???

thanks for any help

Offline spirochete

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Re: Hydroxyacetophenone more acidic than phenol?
« Reply #1 on: December 14, 2008, 11:16:18 AM »
Yes that's correct.  Hydroxyacetophenone being more acidic is consistent with the C=O group being electron withdrawing.  The conjugate base is stabilized by having some of the negative charge delocalized onto the C=O oxygen. 

The effect will be much greater with para and ortho substitution, but some effect is still present in the meta position.  Can you see why?

Offline zephen53

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Re: Hydroxyacetophenone more acidic than phenol?
« Reply #2 on: December 14, 2008, 11:30:45 AM »
would the group on the meta position be less effective because resonance doesnt occur when the group is on the meta?

Offline spirochete

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Re: Hydroxyacetophenone more acidic than phenol?
« Reply #3 on: December 14, 2008, 11:52:26 AM »
That's right.  It has a much smaller effect because it still is electron withdrawing inductively (pulls e- density through sigma bonds).

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