easy OChem Q

[sony102]

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why is OH attached to benzene (phenol) more basic than OR attached to benzene?

 

[doc3232]

why is OH attached to benzene (phenol) more basic than OR attached to benzene?

Well...the R group will donate electrons to the Oxygen making it more negative and hence more basic.
I disagree with your statement.
So you are saying, which is more basic: Ar-OH or Ar-O-R
and these molecules are not at all basic, but rather we are just comparing the two.

Ar=benzene ring

 

[klutzy1987]

why is OH attached to benzene (phenol) more basic than OR attached to benzene?

Wadya mean. Phenol is a stronger acid than methoxybenzene, what makes you say that phenol is more basic.

 

[gentile1225]

i agree with klutz.

 

[xhamburgersamx]

I also agree that -OH is more acidic that -O-R thus OH is less basic than OR

 

[wifi08]

ya klutz is right its the other way around buddy

 

[Chesnok]

Phenol is more acidic than RO-Ar since RO- is a better Nucleophile (since RO-H is weaker acid than water --see pKa's), and, as we know, good Nu's are good bases.
Small explanation in a different way but that works for everything 😉
Good luck

And Always lcompare/look at the leaving groups .

 

[sony102]

Well...the R group will donate electrons to the Oxygen making it more negative and hence more basic.
I disagree with your statement.
So you are saying, which is more basic: Ar-OH or Ar-O-R
and these molecules are not at all basic, but rather we are just comparing the two.

Ar=benzene ring

I thought electron donating groups make benzene more basic than electron withdrawing groups, right? my text book lists OH as a more electron donating group than OR so wouldn't OH make the benzene more basic than OR would?

 

[doc3232]

I thought electron donating groups make benzene more basic than electron withdrawing groups, right? my text book lists OH as a more electron donating group than OR so wouldn't OH make the benzene more basic than OR would?

No, R groups like an ethyl are loaded with electrons and no atoms to pull those electrons because Carbon is not electronegative.
So where do those electrons go? To the Oxygen. As before, Oxygen takes the electrons and becomes more basic.