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Question #44982

Difficulty: 8/10 | 🟢 Free

The Question

2'-Deoxythymidine (initial concentration 0.066 M0.066 \text{ M}) is reacted with a phosphoric acid buffer (total analytical concentration [P]total=0.4 M[P]_{total} = 0.4 \text{ M}) in a specialized solvent system at 298 K298 \text{ K}. The medium is buffered such that the concentration of neutral H3PO4H_3PO_4 is exactly equal to the concentration of its monoanion H2PO4−H_2PO_4^- (assume higher deprotonations are negligible).\n\nIn this medium, only the fully protonated, neutral H3PO4H_3PO_4 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 H3PO4H_3PO_4 are K5=2.0×10−3K_5 = 2.0 \times 10^{-3} and K3=0.5×10−3K_3 = 0.5 \times 10^{-3}, respectively.\n\nTo drive the thermodynamically unfavorable phosphorylation, a molecular sieve apparatus continuously strips water, maintaining its steady-state concentration at 1.0×10−4 M1.0 \times 10^{-4} \text{ M}. 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 (0.4 M0.4 \text{ M}) instead of the active neutral species (0.2 M0.2 \text{ M}) 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

SubjectChemistry
ChapterBiomolecules - Class 12
ConceptNucleoside vs Nucleotide
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree