O Chem Achiever #71

[tawaqul]

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Why are tertiary alcohols more basic than secondary?

 

[tranv117]

just imagine both gaining a proton, making that H2O group a good leaving group. youre then left with a tertiary or secondary carbocation. The tert carbocation is more stable. This makes tert alcohol more basic because it is more likely to pick up that proton.

this is if everything else was equal. ie. #of Cs

 

[polarmolar]

just imagine both gaining a proton, making that H2O group a good leaving group. youre then left with a tertiary or secondary carbocation. The tert carbocation is more stable. This makes tert alcohol more basic because it is more likely to pick up that proton.

this is if everything else was equal. ie. #of Cs

So the e- donating effect of R-groups doesn't factor in?

 

[tranv117]

E- donating effect factors in if there are say 6 Cs vs. 2 Cs. But if youre just looking at tertiary vs. secondary I believe that is the reason.

 

[GCT]

Why are tertiary alcohols more basic than secondary?

Because of the surrounding carbons being electron donating the conjugate base of the teritary alcohol has more repulsion between the oxygen and the attached carbons.