Using 1H NMR Spectroscopy to Study the Free Radical Chlorination of Alkanes

• David Soulsby ^[1]
  1. [1] University of Redlands

     University of Redlands

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 97, Nº 8, 2020, págs. 2286-2290
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • The free radical chlorination of an alkane experiment is often used in the undergraduate laboratory curriculum to introduce students to the free radical mechanism, substituent effects, intermediate stability, and the relative reactivity of radicals. In this experiment, students monochlorinate multiple alkanes and analyze the reaction mixture using 1D 1H NMR spectroscopy. Chemical shift information is provided for characteristic signals for each chlorinated product, and each student then determines product ratios for all of the products to determine reactivity values. This approach allows students to construct a more comprehensive relative reactivity model than is possible when using a single substrate so that they can better understand the role of substituents and their effect on radical stability.