Aniline and cyclohexylamine are both weak organic bases (see equilibria below). If a researcher needed to separate a mixture of the two compounds, which approach should result in the best separation? NH3* NH2 anilinium ion aniline (pKa = 4.6) NH3* NH2 cyclohexylamonium ion cyclohexylamine (pKa = 10.7) O Dissolve the mixture in ether, then extract once with 150 mL of aqueous 0.1 N NaOH O Dissolve the mixture in ether, then extract with three-50mL aliquots of aqueous 0.1 N NaOH O Dissolve the mixture in ether, then extract once with 150 mL of aqueous 0.1 N HCI O Dissolve the mixture in ether, then extract with three-50mL aliquots of aqueous 0.1 N HCI O Dissolve the mixture in ether, then extract once with 150 mL of saturated aqueous bicarbonate solution O Dissolve the mixture in ether, then extract with three-50 mL aliquots of saturated aqueous bicarbonate solution

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Aniline and cyclohexylamine are both weak organic bases (see equilibria below). If a
researcher needed to separate a mixture of the two compounds, which approach should result
in the best separation?
NH3*
NH2
anilinium ion
aniline
(pKa = 4.6)
NH3*
NH2
cyclohexylamonium ion
cyclohexylamine
(pKa = 10.7)
O Dissolve the mixture in ether, then extract once with 150 mL of aqueous 0.1 N NaOH
O Dissolve the mixture in ether, then extract with three-50mL aliquots of aqueous 0.1 N NaOH
O Dissolve the mixture in ether, then extract once with 150 mL of aqueous 0.1 N HCI
O Dissolve the mixture in ether, then extract with three-50mL aliquots of aqueous 0.1 N HCI
O Dissolve the mixture in ether, then extract once with 150 mL of saturated aqueous bicarbonate
solution
O Dissolve the mixture in ether, then extract with three-50 mL aliquots of saturated aqueous
bicarbonate solution
Transcribed Image Text:Aniline and cyclohexylamine are both weak organic bases (see equilibria below). If a researcher needed to separate a mixture of the two compounds, which approach should result in the best separation? NH3* NH2 anilinium ion aniline (pKa = 4.6) NH3* NH2 cyclohexylamonium ion cyclohexylamine (pKa = 10.7) O Dissolve the mixture in ether, then extract once with 150 mL of aqueous 0.1 N NaOH O Dissolve the mixture in ether, then extract with three-50mL aliquots of aqueous 0.1 N NaOH O Dissolve the mixture in ether, then extract once with 150 mL of aqueous 0.1 N HCI O Dissolve the mixture in ether, then extract with three-50mL aliquots of aqueous 0.1 N HCI O Dissolve the mixture in ether, then extract once with 150 mL of saturated aqueous bicarbonate solution O Dissolve the mixture in ether, then extract with three-50 mL aliquots of saturated aqueous bicarbonate solution
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