An Updated Simple SN2 Reaction for the Undergraduate Organic Laboratory

• Kelli S. Khuong ^[1] ; Fabio Agnelli ^[1] ; Matthew A. Parker ^[1]
  1. [1] University of San Diego

     University of San Diego

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 100, Nº 1, 2023, págs. 376-379
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • SN2 reactions are of fundamental importance in introductory organic chemistry courses, and a number of experiments suitable for the first-semester undergraduate organic lab have been previously reported. Most of these experiments have used alkyl halides as electrophiles, but alkyl halides are often less than ideal for reasons of toxicity/volatility and difficulty in TLC visualization. We report an updated methodology utilizing an alkyl tosylate, rather than a halide, as the electrophile. The SN2 reaction of 2-naphthol/sodium hydroxide with butyl p-toluenesulfonate is performed in a single 3 or 4 h lab period and affords a solid product in good yield. The tosylate electrophile gives students experience with a commonly encountered leaving group, is easily visualized on TLC, and has an improved safety profile.