Explain why phenol is more acidic than ethyl alcohol?
Question: Explain why phenol is more acidic than ethyl alcohol?
Phenol is more acidic than ethyl alcohol because the phenoxide ion, which is formed when phenol loses a proton, is more stabilized than the ethoxide ion, which is formed when ethyl alcohol loses a proton.
The phenoxide ion is stabilized by resonance, which means that the negative charge on the oxygen atom is delocalized over the benzene ring. This makes the phenoxide ion less reactive and more stable than the ethoxide ion, which does not have the same delocalization of charge.
In addition, the benzene ring in phenol is electron-withdrawing, which means that it pulls electrons away from the oxygen atom. This makes the oxygen atom more acidic, as it is easier for it to lose a proton.
The combination of resonance stabilization and electron withdrawal makes phenol more acidic than ethyl alcohol.
Here is a diagram of the resonance structures of the phenoxide ion:
O
\
-
/
O
As you can see, the negative charge on the oxygen atom is delocalized over the benzene ring. This makes the phenoxide ion less reactive and more stable than the ethoxide ion.
I hope this explanation is helpful. Let me know if you have any other questions.
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