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May 19, 2025, 11:33:59 pm
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Author Topic: Esters  (Read 698 times)  Share 

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breadkay

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Esters
« on: May 21, 2012, 08:21:09 pm »
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Hi,

Through my research I have found that esters are polar and when they have a short hydrocarbon chain are soluble in water. So, how come an ester like ethyl ethanoate is seen to be insoluble?

Any help is appreciated, as always :)
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IndefatigableLover

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Re: Esters
« Reply #1 on: May 21, 2012, 08:39:59 pm »
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The lack of a Hydroxyl Group (OH) during when it condenses from ethanol and acetic acid therefore makes ethyl ethanoate insoluble. Because it doesn't have any OH groups, it cannot form a water molecule which makes it insoluble although there is a percentage of 3-8% solubility.

http://cavemanchemistry.com/cavebook/chsoap2.html
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breadkay

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Re: Esters
« Reply #2 on: May 21, 2012, 08:44:40 pm »
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Ok.

So it still is soluble, just not to a great extent?
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IndefatigableLover

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Re: Esters
« Reply #3 on: May 21, 2012, 08:47:43 pm »
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Yeah it's solubility is very low
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breadkay

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Re: Esters
« Reply #4 on: May 21, 2012, 08:52:09 pm »
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Awesome, cheers :) :)
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breadkay

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Re: Esters
« Reply #5 on: May 21, 2012, 08:58:57 pm »
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Sorry, got another question, haha :P

How come esters are slightly soluble then? Is it because of the highly electronegative Oxygen in the C=O bond that allows it to Hydrogen bond to some extent?
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Destiny

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Re: Esters
« Reply #6 on: May 21, 2012, 09:18:02 pm »
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Yes, that's what my teacher said :)
As always, the smaller it is, the more soluble it is as the polar functional group exerts a bigger influence on the overall polarity and hence it better dissolves in H2O (polar)
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IndefatigableLover

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Re: Esters
« Reply #7 on: May 21, 2012, 09:23:46 pm »
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Quote from: breadkay on May 21, 2012, 08:58:57 pm
Sorry, got another question, haha :P

How come esters are slightly soluble then? Is it because of the highly electronegative Oxygen in the C=O bond that allows it to Hydrogen bond to some extent?


Unfortunately I am not too sure with myself but I believe it is because the hydrogen bond with C=O is weak therefore it is soluble. It is not just the C=O that can have a Hydrogen bond with water as alcohol (OH) has a weak hydrogen bond with water which makes it soluble.

http://www.chemguide.co.uk/organicprops/esters/background.html
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