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Today I completed an organic lab practical test about discontinuous extraction. I had to extract succinic acid from a water solution using ethyl acetate as the solvent extractor. After the extraction, I calculated the partition coefficientto be 0.3. So, succinic acid is more soluble in water than ethyl acetate, but why?

Does it have to do with the ionization of the succinic in water that may not be possible in ethyl acetate or its related to the intermolecular interations?

strutucture of ethyl acetate

structure of succinic acid

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Hydrogen bonding interactions are also much stronger between succinic acid and water as opposed to EA since EA doesn't have any H-atoms that can participate in the hydrogen bonding.

Ionization is also a significant point to consider, but without pH data we can't say for sure.

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  • $\begingroup$ This reads more like a comment than an answer. Consider adding more detail or it may be deleted. $\endgroup$ – bon Apr 22 '16 at 9:10
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Unless you solved something basic to your water only a small fraction of your succinic acid will ionize, so my guess is water can have more interactions with succinic acid than ethyl acetate which makes sense because water is small.

The partition coefficient is very pH dependent in this case. If you would ionize succinic acid it would have a near 100% selectivity for water.

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