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  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > April  >
In the Laboratory
Competitive Nitration of Benzene–Fluorobenzene and Benzene–Toluene Mixtures: Orientation and Reactivity Studies Using HPLC
Ronald L. Blankespoor, Stephanie Hogendoorn, and Andrea Pearson
Department of Chemistry & Biochemistry, Calvin College, Grand Rapids, MI 49546-4388
Cover
April 2007
Vol. 84 No. 4
p. 697

Abstract
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.
Supplement
HPLC equipment and conditions used in this experiment, analyses of the chromatographic data, instructions for the students and notes for the instructor are available.
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Citation
Blankespoor, Ronald L.; Hogendoorn, Stephanie; Pearson, Andrea. J. Chem. Educ. 2007, 84, 697.
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Keywords
Aromatic Compounds; Constitutional Isomers; Electrophilic Substitution; Hands-On Learning / Manipulatives; HPLC; Laboratory Instruction; Organic Chemistry; Second-Year Undergraduate
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History
Created:
Last Updated:
3/6/2007
3/8/2007
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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