TOJC: 10.9

rossjm@plu.edu
Sun, 01 Dec 1996 17:53:27 -0800 (PST)

Lori
I think your confusion may be in your understanding of solvation.
When the alkoxide ion is solvated, it is merely surrounded by the
molecules of solvent. The molecules of solvent stabilize the ion. Now for
the reaction you see near the top of page 434 to occur the alkoxide ion
must be somewhat stable or else only the reverse of this reaction would
occur. If you notice the arrows in the reaction indicate that the
equilibrium lies further to the right (towards the alcohol and water).
This implies to me that the formation of an alkoxide ion is not favored,
and when the R group of the alcohol is bulky this reaction most likely
will not take place at all. (A bulky R group is not effectively stabilized
by solvation.)

If anyone has anything else to add or corrections please respond.

Hope this helps, Lori.

J M Ross

On Sun, 1 Dec 1996, Lori wrote:

>
> Question for any of you great chem people...
> In section 10.9, I am wondering why solvation would stabilize an
> alkoxide ion, because doesn't that mean it's creating a - charge? Why
> would this be more stable than when it's neutral? Or am I just thinking
> wrong? I'm confused on this part, so any help would be great! Hope all
> your Thanksgivings were wonderful!
>
> { Lori Grimberg | We trust, sir, that God is on our side. }
> { Grimbele@pepper.plu.edu | It is more important to know that we are }
> { Student Consultant | on God's side. -ABRAHAM LINCOLN }
>
>