Why can't alcohol react with aqueous NaOH?

[fluppocinonys]

Hi, alcohol 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 salt too?

Many thanks!

 

[Ygggdrasil]

The reaction will, in fact occur. The correct formula would be:

NaOH + R-OH --> R-ONa + H₂O

or if you prefer the net ionic equation:

OH^- + R-OH --> R-O^- + H₂O

where R-OH represents the alcohol. So, in this case, it's the hydroxide reacting with the alcohol, not the sodium ions. The sodium ions are just a spectator in the reaction.

The free energy difference between the products and reactants side of the equation is not very large, however, so there will be some equilibrium between hydroxide ions (OH^-) and alkoxide ions (R-O^-) in solution, which will depend on the pKa of the alcohol.

 

[Borek]

Note that alkoxides are usually bases strong enough to deprotonate water, so if there is water present, you end with alcohol and OH^-.

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