Session S41a (Tuesday, 9:30am, Wartik 110)

P392: Practical improvement to the resolution of (±)-1-phenylethylamine

Daniel Clark, Jonathan Touster (Clarion University of Pennsylvania, USA)

Polarimetry and optical purity are often introduced in organic chemistry laboratory with the resolution of (±)-1-phenylethylamine using (+)-tartaric acid as the resolving agent.  As traditionally performed there are several drawbacks to this experiment owing to the isolation and analysis of the resolved, neat (–)-1-phenylethylamine.  First, we have found that with a miniscale procedure, the amount of resolved amine by each individual student is of insufficient volume and purity for direct analysis by polarimetry.  Furthermore, we have found the neat amine malodorous and relatively reactive with the carbon dioxide in the air.  We have developed a practical improvement to the final steps of this experiment by directly analyzing the combined organic extracts containing the resolved amine, thereby avoiding the problematic neat amine.  This process employs a refractometer to determine the concentration of the resolved amine with subsequent analysis with a polarimeter to determine the optical purity.


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