Propylene Oxide Addition to Hydrochloric Acid:: A Textbook Error

• Rebecca E. Phillips ^[1] ; Robert L. Soulen ^[1]
  1. [1] Southwestern University

     Southwestern University

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 72, Nº 7 (July), 1995, págs. 624-625
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • Many current textbooks suggest that, in contrast to base catalyzed epoxide ring opening, acid catalyzed epoxide ring opening reactions proceed via a carbocation intermediate with nucleophilic attack at the more hindered carbon. However, we show that slow addition of propylene oxide to concentrated or dilute hydrochloric acid yields predominantly 1 -chloro-2-propanol and a smaller amount of 2-chloro-1 -propanol. The reaction may be varied by addition of inert solvents or by the addition of sodium bromide to demonstrate changes in the mechanism ( Sn-1 versus Sn-2) and nucleophilic competition.