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Selective and Quantitative Catalytic Hydrogenation: A Safe, Inexpensive Experiment for Large Classes
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Abstract
Students measure the rate of hydrogenation of 4-vinylcyclohexene in the presence of an inexpensive, non-pyrophoric nickel boride (PI) catalyst prepared from nickel(II) acetate and sodium borohydride. The vinyl group hydrogenates rapidly followed by the distinctly slower hydrogenation of the cyclohexene. An atmospheric hydrogenation apparatus for the experiment is easily constructed from a 50-mL buret, a rubber thermometer adapter, a small pear-shaped flask, two short Pasteur pipets, two small syringe caps, a leveling bulb or separatory funnel, a small rubber stopper, and some Tygon tubing.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
CatalysisCiting Articles
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
An Undergraduate Organic Chemistry Laboratory: The Facile Hydrogenation of Methyl trans-Cinnamate
Kenneth J. O’Connor, Kimberly Zuspan, and Lonnie BerryJournal of Chemical Education2011 88 (3), 325-327An Undergraduate Organic Chemistry Laboratory: The Facile Hydrogenation of Methyl trans-Cinnamate
Kenneth J. O’Connor, Kimberly Zuspan, and Lonnie BerryJournal of Chemical Education2011 88 (3), 325-327Hydrogenation of alkenes is an important reaction in the synthesis of organic molecules. In this experiment, students conduct a high-yield microscale hydrogenation reaction of methyl trans-cinnamate using a readily available, safe, and convenient hydrogen ...
Catalytic Hydrogenation of Maleic Acid at Moderate Pressures
Kwesi AmoaJournal of Chemical Education2007 84 (12), 1948Catalytic Hydrogenation of Maleic Acid at Moderate Pressures
Kwesi AmoaJournal of Chemical Education2007 84 (12), 1948Moderate-pressure catalytic hydrogenation is often overlooked as a classroom demonstration because of the awkwardness of the equipment and the time constraints required for the conversion of reactants to products. This article demonstrates the reduction ...
Incorporating Guided-Inquiry Learning into the Organic Chemistry Laboratory
Allen M. Schoffstall , Barbara A. GaddisJournal of Chemical Education2007 84 (5), 848Incorporating Guided-Inquiry Learning into the Organic Chemistry Laboratory
Allen M. Schoffstall , Barbara A. GaddisJournal of Chemical Education2007 84 (5), 848Informed science educators who are responsible for undergraduate laboratory programs strive to improve the effectiveness of learning in the laboratory. Guided-inquiry learning in the laboratory is one reasonable alternative (among others described here) ...
Combinatorial Partial Hydrogenation Reactions of 4-Nitroacetophenone. An Undergraduate Organic Laboratory
Kevin W. Kittredge , Susan S. Marine and Richard T. TaylorJournal of Chemical Education2004 81 (10), 1494Combinatorial Partial Hydrogenation Reactions of 4-Nitroacetophenone. An Undergraduate Organic Laboratory
Kevin W. Kittredge , Susan S. Marine and Richard T. TaylorJournal of Chemical Education2004 81 (10), 1494A combinatorial organic chemistry experiment that utilizes an inexpensive commercially available parallel reactor, Argonaut's FirstMate, is described. Students perform a metal catalyzed partial hydrogenation reaction on a multi-functionalized substrate ...
Catalytic Hydrogenation of Organic Compounds without H2 Supply: An Electrochemical System
Daniela Maria do Amaral Ferraz Navarro and Marcelo NavarroJournal of Chemical Education2004 81 (9), 1350Catalytic Hydrogenation of Organic Compounds without H2 Supply: An Electrochemical System
Daniela Maria do Amaral Ferraz Navarro and Marcelo NavarroJournal of Chemical Education2004 81 (9), 1350A system for hydrogenation of organic compounds without a hydrogen gas supply is described. The process involves an electrochemical apparatus for the generation of hydrogen in situ. The simplicity of the experiment allows students to carry out easy ...
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- Received: August 03, 2009
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