[Lynda92]

Hi everyone,

I have a question: Methanol has a Pka of 15.54 and triethylamine has a Pka of 10.75. Does this mean that methanol is a stronger base than triethylamine and therefore is more likely to accept a proton? Also is methanol a better nucleophile?

Thanks

[mjc123]

Triethylamine has no acidic protons and no pKa (or a very high one). I think you mean pKa of Et₃NH⁺ is 10.75. The pKa of a compound is a measure of the acidity, not the basicity, of that compound. It reflects the basicity of the conjugate base (which may be very different from that of the original compound). Your numbers tell you that Et₃NH⁺ is a stronger acid than MeOH, and therefore that MeO^- is a stronger base than Et₃N. They do not tell you about nucleophilicity.