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Question #44982
The Question
2'-Deoxythymidine (initial concentration ) is reacted with a phosphoric acid buffer (total analytical concentration ) in a specialized solvent system at . The medium is buffered such that the concentration of neutral is exactly equal to the concentration of its monoanion (assume higher deprotonations are negligible).\n\nIn this medium, only the fully protonated, neutral species acts as the active electrophile for the nucleophilic acyl-like substitution by the nucleoside hydroxyl groups. The equilibrium constants for the formation of the 5'-phosphoester and 3'-phosphoester from neutral are and , respectively.\n\nTo drive the thermodynamically unfavorable phosphorylation, a molecular sieve apparatus continuously strips water, maintaining its steady-state concentration at . Assuming no other side reactions occur, what is the equilibrium concentration of the 5'-nucleotide (thymidine-5'-monophosphate)?
Options
- A.
0.044 \text{ M}
- B.
0.048 \text{ M}
- C.
0.011 \text{ M}
- D.
0.053 \text{ M}
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Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Numerical_Precision
Improve calculation stamina and avoid rounding errors in high-stakes competitive examinations.
Concepts Behind This Question
Nucleoside vs Nucleotide|Nucleophilic Acyl Substitution|Esterification Reversibility
Why This Question Is Tricky
Common Mistakes
This problem tests the thermodynamic principles of nucleophilic acyl substitution applied to biological molecules (phosphorylation).
The primary trap is failing to account for the speciation of phosphoric acid; students who use the total phosphate concentration () instead of the active neutral species () will incorrectly calculate a ratio of 8:1, leading to Option B.
Furthermore, it tests Le Chatelier's principle in esterification: water is a product, and its steady-state concentration dictates the equilibrium position.
Finally, it requires setting up a simultaneous mass balance equation that accounts for regioselectivity (primary 5'-OH vs secondary 3'-OH) and unreacted starting material.
Ignoring the unreacted nucleoside leads to Option D, while confusing the regioselectivity leads to Option C.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Biomolecules - Class 12 |
| Concept | Nucleoside vs Nucleotide |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |