Benzyl and Pheny

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MedHopeful234

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10+ Year Member
Sorry for the lacking L in the title

Are benzene groups electron withdrawing or donating? What about phenyl groups?

I'm asking regarding acidity of benzoic acid and acetic acid...Destroyer states that halogens, No2, benzene rings...etc. are all electron donating. But that contradicts benzoic acid being a strong acid in comparison to acetic acid. Benzene would have to be electron withdrawing for it to cause benzoic acid to be more acidic than acetic acid (electron withdrawing groups decrease basicity but increase acidity).
 
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Yes. Destroyer is correct. Benzoid acid has COOH group, which is electron withdrawing. Has nothing to do with benzene itself.
 
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Thanks Dotoday... I guess what I needed clarification on is how do benzene and phenyl act as substituents? EW or ED?

Also, acetic acid has a COOH group that is electron withdrawing too... so it must have to do with the difference in benzene vs. CH3 group attached to the COOH
 
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Yes. When a COOH group is attached to the Benzene ring, it is stabilized by resonance. When a COOH is attached to CH3, there is no extra resonance stabilization.
 
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