HPLC Separation of Phenacetin, Salicylic Acid, Nicotine, Methylamphetamine, and Phenobarbatuic Acid

The graph shown below is a plot of retention time vs. pH for the reverse-phase HPLC separation of a mixture containing phenacetin, salicylic acid, nicotine, methylamphetamine, and phenobarbituic acid.

Based on the structures of these compounds and their pKa values, match each compound to one of the five curves.  Be sure to clearly justify your reasoning.

About the Author

ASDL Contributor

David Harvey

Professor of Chemistry & Biochemistry at DePauw University

David T. Harvey is a Professor Emeritus of Chemistry and Biochemistry at DePauw University in Greencastle, Indiana, where he has been a dedicated faculty member since 1986. Over his nearly four-decade career, Dr…
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