Solvent Extraction question at different pH levels

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SUMMARY

The discussion focuses on the solvent extraction of specific compounds—CH3CH2COOH, CH3CH2NH2, CH3CH2CH2OH, and H2NCH2CH2COOH—at pH levels of 12 and 2. It establishes that the dominant form of each compound is determined by comparing their pKa values to the pH; compounds are protonated at lower pH and deprotonated at higher pH. The key conclusion is that only neutral species can effectively extract into hexane, confirming that charge plays a crucial role in the extraction process.

PREREQUISITES
  • Understanding of acid-base chemistry and pKa values
  • Familiarity with solvent extraction techniques
  • Knowledge of the properties of organic compounds
  • Basic grasp of pH and its effects on chemical species
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  • Research the pKa values of common organic acids and bases
  • Explore solvent extraction methods in organic chemistry
  • Learn about the effects of pH on solubility and extraction efficiency
  • Investigate the role of charge in the solubility of compounds in organic solvents
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Chemistry students, organic chemists, and professionals involved in solvent extraction processes will benefit from this discussion.

H98_
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The question I have been given:
Draw the dominant forms of each of the compounds below and state which, if any, would be expected to extract from aqueous solution into hexane at (a) pH 12 and (b) pH 2. CH3CH2COOH CH3CH2NH2 CH3CH2CH2OH H2NCH2CH2COOH
From my understanding, I can tell what the dominant form is by comparing the pKa of each compound to the pH; if the pH is lower, the specie is protonated. If it is higher, the specie is deprotonated. I am confused on how to tell whether it will extract into hexane? Is it based on whether the specie is charged or not (a neutral specie is the only one that will extract into hexane)?
 
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H98_ said:
Is it based on whether the specie is charged or not (a neutral specie is the only one that will extract into hexane)?

Yes.
 
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