Hydrolysis of ethyl ethanoate (soaponification)

knarl

Gday Guys,

OK, I have a few queries regarding the hydrolysis of ethyl ethanoate:

Firstly, hydrolysing ethyl ethanoate(acetate) using sodium hydroxide solution:

CH3COOCH2CH3 + NaOH ----> CH3COONa + CH3CH2OH
ethyl ethanoate sodium hydroxide sodium ethanoate ethanol

Would I be right to think using bicarb (NaHCO3) would change the reaction to this (I'm just drawing from highschool chem that was a few years ago):?

CH3COOCH2CH3 + NaHCO3 ----> CH3COONa + CH3CH2OH + CO2

In the same way bicarb produces CO2 in its acid base reactions???

If so, do you think it would be a fast reaction to hydrolyse traces of ethyl ethanoate in a solution of 40% ethanol by volume in water by adding excess sodium bicarbonate and heating to boiling?

Cheers,
knarl.

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I doubt that NaHCO₃ would be very efficient at ester hydrolysis. It's not very nucleophilic, while with NaOH you have OH- to act as the nucleophile. In the acidic decomposition of carbonate you protonate on of the OH to make OH₂+, which is then a good leaving group, so the mechanism is different.