Hydrolysis of ethyl ethanoate (soaponification)

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SUMMARY

The discussion centers on the hydrolysis of ethyl ethanoate (acetate) using sodium hydroxide (NaOH) and sodium bicarbonate (NaHCO3). The reaction with NaOH produces sodium ethanoate and ethanol, while the proposed reaction with NaHCO3 is less efficient due to its lower nucleophilicity. Participants conclude that NaHCO3 is not suitable for effective ester hydrolysis, as it does not provide a strong enough nucleophile compared to hydroxide ions from NaOH.

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  • Basic principles of acid-base chemistry
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knarl
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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 high school 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.
 

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