Ciprofloxacin has a carboxylic acid group of pKa 6.09 and a secondary amine group of pKa 8.74. Using the Henderson-Hasselbalch equation, determine determine which functional groups of the molecule will be ionized in the stomach (pH 1) and in the colon (pH 6). Show your calcultions. It is not necessary to calculate the degree of ionization. HN, pka 8.74 Ciprofloxcin COOH pka 6.09

Principles of Modern Chemistry
8th Edition
ISBN:9781305079113
Author:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Publisher:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Chapter15: Acid–base Equilibria
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QUESTION 11
Ciprofloxacin has a carboxylic acid group of pKa 6.09 and a secondary amine group of pKa 8.74. Using the Henderson-Hasselbalch equation, determine determine which functional groups of the molecule will be
ionized in the stomach (pH 1) and in the colon (pH 6). Show your calcultions. It is not necessary to calculate the degree of ionization.
HN
pka 8.74
F
`N
Ciprofloxcin
`N
COOH
pka 6.09
Transcribed Image Text:QUESTION 11 Ciprofloxacin has a carboxylic acid group of pKa 6.09 and a secondary amine group of pKa 8.74. Using the Henderson-Hasselbalch equation, determine determine which functional groups of the molecule will be ionized in the stomach (pH 1) and in the colon (pH 6). Show your calcultions. It is not necessary to calculate the degree of ionization. HN pka 8.74 F `N Ciprofloxcin `N COOH pka 6.09
Expert Solution
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Due to the acidic nature of carboxylic acids, their level of dissociation is directly related to the pH of the solution. Under acidic conditions (low pH), carboxylic acids are almost completely undissociated and exist primarily in their protonated form (RCOOHRCOOH). Under, basic conditions (high pH), carboxylic acids become nearly completely dissociated into their deprotonated carboxylate form (RCOORCOO). Because the environment inside a living cell is an aqueous buffer with a nearly neutral pH = 7.3 (sometimes referred to as the physiological pH

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