Competitive Nitration of Benzene Fluorobenzene and Benzene Toluene Mixtures: Orientation and Reactivity Studies Using HPLC.

• Autores: Ronald L. Blankespoor, Stephanie Hogendoorn, Andrea Pearson
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 84, Nº 4, 2007, págs. 697-698
• Idioma: inglés
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• Resumen

  • In this experiment for the first-year organic laboratory mixtures of benzene�toluene and benzene�fluorobenzene are competitively nitrated using HNO3�acetic anhydride to determine the reactivity and orientation effects of CH3 and F, respectively. This experiment accomplishes the goals of studying these effects in a single laboratory session and using HPLC to analyze the reaction mixtures. Approximately one-half of the students nitrate the benzene�toluene mixture and find that the CH3 group activates and directs ortho�para. The other half nitrate the benzene�fluorobenzene mixture and find that fluorine deactivates slightly and directs ortho�para with a ratio much less than the statistically expected 2:1 value.