Homework Help: Organic Chemistry

Posted by Bethany on Saturday, February 16, 2008 at 4:36pm.

Alcohol has OH functionality, but do you expect it to be a base and why?

I would expect it to be a base, but I am not sure why. Does anyone know?

Organic Chemistry - DrBob222, Saturday, February 16, 2008 at 5:07pm
To be a base, the molecule (oxygen atom in this case) must ACCEPT a proton. How many reactions do you know in which the OH part of say, CH3OH or C2H5OH, accepts a proton to become CH3OH2^+ or C2H5OH2^+. I don't know of any. In organic chemistry, the -NH2 group is a base BECAUSE the N atom has an extra pair of electrons AND because a H^+ can add to those two electrons. These boards don't allow us to draw electron dot structures but I'll try to show an amine adding a H^+.

   H
   ..
R:N:H
   ..

See the two unused electrons at the bottom of the RNH2 compound. Those two electrons can accept a hydrogen ion, and they do, to form the amine salt, RNH3^+.
I hope this is clear to you but if it isn't please post a follow up question. If the spacing doesnt work out on the electron dot structure, I did the best I could.
- Organic Chemistry - DrBob222, Saturday, February 16, 2008 at 5:08pm
  Actually, the electron structure looks pretty good. That't about as good as it gets on these boards.
Organic Chemistry - Bethany, Saturday, February 16, 2008 at 5:23pm
Thank-you for taking the time to help me understand the question.

I think I understand, would the following statement be correct:

Alcohol would not be a base, because in order to be a base the molecule must accept a proton.
- Organic Chemistry - DrBob222, Saturday, February 16, 2008 at 6:28pm
  That would sound good to me.

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