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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 65AP: Phenacetin, a substance formerly used in over-the-counter headache remedies, has the formula...

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