October 28, 2021, 04:54:51 PM
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Topic: Hydrolysis??  (Read 278 times)

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Offline myii

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Hydrolysis??
« on: May 16, 2021, 03:10:55 AM »
Hi guys :)

Just wondering: whether the values of kOH and kNH3 for the hydrolysis of ethyl fluoroacetate would be higher or lower than those for the hydrolysis of ethyl chloroacetate.

It would be higher right, due to the increase rate of reaction from the hydrolysis of ethyl fluoroacetate?

Offline Orcio_Dojek

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Re: Hydrolysis??
« Reply #1 on: May 16, 2021, 06:46:18 AM »
Hydrolysis rate of ester depends on concentration of hydrolysed compound + concentrations of H+ or OH-, as both ions accelerate reaction rate.

Ethyl fluoroacetate should be more reactive towards OH-, as fluorine atom make carbonyl carbon more electrophilic, so reaction rate should be higher.


Offline Orcio_Dojek

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Re: Hydrolysis??
« Reply #2 on: May 16, 2021, 11:35:35 AM »
Quote
whether the values of kOH and kNH3 for the hydrolysis of ethyl fluoroacetate would be higher or lower than those for the hydrolysis of ethyl chloroacetate.

kOH (rate constant of hydrolysis) should be higher for ethyl fluoroacetate.

Second page:

https://web.viu.ca/krogh/chem331/Hydrolysis%20Lab%202006.pdf

Hydrolysis constant of CHCl2-COOCH3 is higher than CH3-COOCH2CH3.

As of kNH3 (rate constant of amide formation - side reaction of hydrolysis in ammonia solution) I think it also should be higher as both reactions follows the same mechanism.
« Last Edit: May 16, 2021, 12:31:09 PM by Orcio_Dojek »

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