Higher Rf Value? (TLC Chromatograpghy)

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SUMMARY

The discussion centers on the Rf values of acetaminophen and phenacetin during TLC chromatography using silica gel and a nonpolar solvent. Acetaminophen exhibits a higher Rf value due to its phenolic group, which makes it less polar compared to phenacetin, which contains an aromatic ether. The polarity of the compounds significantly influences their separation on the TLC plate, with acetaminophen being less polar and thus traveling further in the nonpolar solvent.

PREREQUISITES
  • Understanding of TLC (Thin Layer Chromatography) principles
  • Knowledge of polarity and its effect on chromatography
  • Familiarity with chemical structures of acetaminophen and phenacetin
  • Basic grasp of solvent interactions in chromatography
NEXT STEPS
  • Study the impact of solvent polarity on Rf values in TLC
  • Learn about the structural differences between phenolic compounds and aromatic ethers
  • Explore the use of different developing solvents in TLC for varying results
  • Investigate the role of molecular weight in chromatographic separation
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Chemistry students, laboratory technicians, and researchers involved in organic chemistry and chromatographic techniques.

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Homework Statement


Suppose you carry out a TLC separation of acetaminophen and phenacetin on silica gel using a nonpolar developing solvent. Which should have the higher Rf value, and why?


Homework Equations


Im not sure. Is polarity a factor here? I don't think the polarity difference is that great here. Could molecular weight play a factor?


The Attempt at a Solution

 
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It is mostly polarity. Look at the structures! Both structures contain the same aromatic acetamide functionality but Acetaminophen has a phenolic group whereas phenacetin has an aromatic ether on the aromatic ring. Can you estimate which will be most polar and least polar?
 

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