An Undergraduate Organic Chemistry Laboratory: The Facile Hydrogenation of Methyl trans-Cinnamate

• Kenneth J. O'Connor ^[1] ; Kimberly Zuspan ^[1] ; Lonnie Berry ^[1]
  1. [1] Marshall University

     Marshall University

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 88, Nº 3, 2011, págs. 325-327
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • Hydrogenation of alkenes is an important reaction in the synthesis of organic molecules. In this experiment, students conduct a high-yield microscale hydrogenation reaction of methyl trans-cinnamate using a readily available, safe, and convenient hydrogen source. The conditions are similar to those seen in an organic chemistry textbook for an alkene hydrogenation: 5% Pd/C catalyst, 1 atm H2, and room temperature. Students learn how to monitor the change in hydrogen pressure versus time using a Vernier LabQuest and a gas pressure sensor during the 45 min reaction time. The hydrogenation apparatus is easily constructed in 5 min. Students are able to demonstrate using the ideal gas law that the amount of alkene hydrogenated is equal to the decrease in hydrogen pressure. The structure of the saturated ester is confirmed by 1H NMR spectroscopy.