Hydrolysis of ethyl ethanoate (soaponification)

  • Thread starter knarl
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In summary, the conversation discusses the hydrolysis of ethyl ethanoate using sodium hydroxide and bicarbonate. The use of bicarbonate is not as efficient as sodium hydroxide due to its lower nucleophilic properties. The acidic decomposition of carbonate also has a different mechanism compared to the hydrolysis using sodium hydroxide.
  • #1
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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  • #2
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.
 
  • #3


Hi knarl,

Yes, you are correct in thinking that using bicarbonate (NaHCO3) would change the reaction to produce CO2 gas. This is because bicarbonate is a weaker base compared to hydroxide, so it will not completely hydrolyze the ethyl ethanoate into sodium ethanoate and ethanol. Instead, it will form a carboxylate salt (sodium ethanoate) and carbonic acid, which then decomposes into CO2 and water.

As for the reaction being fast, it really depends on the concentration of ethyl ethanoate and the amount of bicarbonate added. If there are only traces of ethyl ethanoate, it may take some time for the reaction to occur, but it should eventually produce CO2 gas. Heating to boiling may help speed up the reaction, but it is not necessary.

Hope this helps!
 

What is hydrolysis of ethyl ethanoate?

Hydrolysis of ethyl ethanoate, also known as saponification, is a chemical reaction in which ethyl ethanoate (also called ethyl acetate) is broken down into its component molecules, ethanoic acid (acetic acid) and ethanol, in the presence of water and a strong base.

What is the purpose of saponification?

Saponification is commonly used in the production of soap, as it is the process by which fats and oils are converted into soap molecules called sodium or potassium salts. It is also used in the production of esters, a common type of chemical compound.

What are the products of hydrolysis of ethyl ethanoate?

The products of hydrolysis of ethyl ethanoate are ethanoic acid (acetic acid) and ethanol. These molecules are formed through the breaking of the ester bond in ethyl ethanoate, resulting in the release of ethanoic acid and ethanol.

What is the mechanism of saponification?

The mechanism of saponification involves the nucleophilic attack of hydroxide ions on the carbonyl carbon in the ester, breaking the ester bond and forming an unstable intermediate. This intermediate then undergoes protonation and deprotonation steps, resulting in the formation of ethanoic acid and ethanol.

What are the factors that affect the rate of saponification?

The rate of saponification can be affected by several factors, including the concentration of the reactants (ethyl ethanoate, water, and base), temperature, and the presence of catalysts. Higher concentrations and temperatures typically result in faster reactions, while the presence of catalysts can speed up the reaction without being consumed in the process.

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