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Kinetic Study of the Heck Reaction: An Interdisciplinary Experiment

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Christel Gozzi and Naoual Bouzidi

Laboratoire de Chimie Organometallique de Surface (LCOMS), Ecole Supérieure de Chimie Physique Electronique de Lyon (CPE Lyon), Villeurbanne cedex, France

J. Chem. Educ., 2008, 85 (8), p 1126

DOI: 10.1021/ed085p1126

Publication Date (Web): August 1, 2008

Abstract

The aim of this experiment is to study and calculate the kinetic constant of a Heck reaction: the arylation of but-3-en-2-ol by iodobenzene catalyzed by palladium acetate in presence of triethylamine in DMF. The reaction leads to a mixture of two ketones. Students use GC analysis to quantify reagents and products of reaction. They control the global order of the reaction and prove that the two products are formed by two reactions that are in parallel. Finally, they calculate the rate constant for each reaction. Students calculate iodobenzene conversion, each product selectivity, yield, and catalyst turn over number (TON). These calculations are controlled using an internal standard, (-)-fenchone. This experiment is completed by students during their second-year kinetic laboratory and is done in pairs in a four-hour laboratory. This work allows students to work in the fields of organic and analytical chemistry, catalysis, and kinetics at the same time.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Analytical Chemistry

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Aromatic Compounds

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