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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Atarijedi on June 14, 2021, 12:56:19 AM

Title: Can the hydroxides created by Sodium carbonate in water, hydrolyse esters?
Post by: Atarijedi on June 14, 2021, 12:56:19 AM

Let's say I have a 1L solution of 50% water, 45% ethanol, and 5% ethyl acetate.

I then put 10g of Sodium carbonate into it. After dissociation, that carbonate will accept a proton from a water molecule, turning into a bicarbonate and also producing a hydroxide.

Then it is possible that the bicarbonate will accept a proton from water turning into carbonic acid, and also producing a hydroxide. The carbonic acid would then decompose into water and carbon dioxide.

1. CO3(2-) + H2O  ::equil:: HCO3- + OH-

2. HCO3- + H2O  ::equil:: H2CO3 + OH-

3. H2CO3 :rarrow: H2O + CO2

So if an ester or alcohol is present, is it possible that the hydroxide produced will end up hydrolysing the ester, or deprotonating the alcohol, instead of participating in the equilibrium reactions?

I guess I'm wondering if sodium carbonate, even though it can't do it directly, can indirectly cause base hydrolysis of an ester.

Title: Re: Can the hydroxides created by Sodium carbonate in water, hydrolyse esters?
Post by: rolnor on June 14, 2021, 03:32:48 AM

I think it can, its a matter if speed. If you have a sensitive ester like p-NO2Phenyl it can be fast. Also if you boil the solution it can be significant.