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Hydrolysis of ethyl ethanoate (soaponification)

  1. Jul 5, 2005 #1
    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.
     
  2. jcsd
  3. Jul 5, 2005 #2

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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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