Fundamentals of Organic ChemistryChemistryBiomolecules
Which of the following best represents the predominant structure of alanine in the bloodstream (a buffered solution at approximately pH 7.4)? The p K_ a values for alanine are 2.3 ( - CO ₂ H ) and 9.7 ( - NH ₃^+ ).
Correct answer
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Step-by-step solution
The pH of the bloodstream is 7.4 . For the carboxylic acid group, the p K_ a is 2.3 . Since pH > p K_ a , this group exists predominantly in its deprotonated form, - CO ₂^- . For the amino group, the p K_ a is 9.7 . Since pH Thus, alanine exists as a zwitterion containing both - NH ₃^+ and - CO ₂^- groups. Structure (A) correctly represents this zwitterionic form. Answer: