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
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
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
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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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F2f355f0d-6bad-496d-affc-f6c8ffbc9dbd%2F430be7a9-de6e-4471-b7bf-bd0e64d0d3a0%2F032225.jpeg&w=3840&q=75)
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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