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Competitive Nitration of Benzene–Fluorobenzene and Benzene–Toluene Mixtures: Orientation and Reactivity Studies Using HPLC
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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.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Aromatic CompoundsCiting Articles
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This article has been cited by 1 ACS Journal articles (1 most recent appear below).
Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course
Patricia Demare and Ignacio ReglaJournal of Chemical Education2012 89 (1), 147-149Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course
Patricia Demare and Ignacio ReglaJournal of Chemical Education2012 89 (1), 147-149This article describes one of the projects in the advanced undergraduate organic chemistry laboratory course concerning the synthesis of two local anesthetic drugs, prilocaine and benzocaine, with a common three-step sequence starting from toluene. ...
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- Received: August 03, 2009
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