[123456789]

Ethanol is able to react with Na (s), but not NaOH (aq)
Why is it so?
In aqueous NaOH, there are mobile Na+ and OH-, so shouldn't alcohol be able to react with Na+ to form water and salt too, as it can be considered as an acid?

[Guitarmaniac86]

They do react but the problem is, the alcohol reforms.

The aqueous NaOH reacts with your alcohol to form C-O^-Na⁺ and water. The ethoxide ion will react with... water reforming the alcohol. These are in equilibrium so effectively, the net reaction is no reaction because the ethanol reforms.

Also, the pKa of sodium hydroxide may not be high enough to deprotonate ethanol to form your ethoxide... However, I cannot find a decent pKa table to compare the pKa of ethanol with sodium hydroxide.

[orgopete]

You should be able to calculate the equilibrium amount of NaOEt and H2O present if solid NaOH were added to ethanol.

[AWK]

http://faculty.swosu.edu/william.kelly/pdf/ch17.pdf

[AC Prabakar]

http://faculty.swosu.edu/william.kelly/pdf/ch17.pdf

nice study material! Thanks for sharing....

[Babcock_Hall]

http://faculty.swosu.edu/william.kelly/pdf/ch17.pdf

There is some very good material here, but there is also a typo.  "The O-H and S-H bonds of alcohols and thiols are able to undergo homolytic cleavage to give a proton and the conjugate base."  The author must mean heterolytic cleavage.

[helper]

This material is very helpfull! Thank you!

[AlphaScent]

Just printed that.

Thanks AWK!!

[Altered State]

Related useful stuff:

http://evans.harvard.edu/pdf/evans_pka_table.pdf