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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > May  >
In the Laboratory
Intermolecular and Intramolecular Forces: A General Chemistry Laboratory Comparison of Hydrogen Bonding in Maleic and Fumaric Acids
Frazier W. Nyasulu and John Macklin
Department of Chemistry, University of Washington, Seattle, WA 98195-1700
Cover
May 2006
Vol. 83 No. 5
p. 770
Abstract
This article presents a simple laboratory experiment that is designed to enhance students' understanding of inter- and intramolecular hydrogen bonding by demonstrating the comparative effect of these phenomena on some chemical and physical properties. Ball-and-stick molecular models are built and used for the consideration of hydrogen bonding possibilities in cis-1,2-dicarboxyethene (maleic acid) and trans-1,2-dicarboxyethene (fumaric acid). On the basis of the expected relative strengths of inter- and intramolecular hydrogen bond associations, students predict which of the two compounds has the higher melting point, higher first acid ionization constant, and higher second acid ionization constant. Appropriate measurements are then performed and used to identify which of a pair of compounds is maleic acid. Students are given standard enthalpies of sublimation, formation, combustion, and hydrogenation and asked to consider their relative values based on intra- and intermolecular hydrogen bonding.
Supplement
Instructions for the students with notes for the instructor interspersed and a report sheet are available.
*  Contents JCE2006p0770W.doc (Microsoft Word)
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*  Citation
 Nyasulu, Frazier W.; Macklin, John. J. Chem. Educ. 2006 83 770.
*  Keywords
 Acids / Bases; First-Year Undergraduate / General; Hands-On Learning / Manipulatives; Hydrogen Bonding; Inquiry-Based / Discovery Learning; Laboratory Instruction; Noncovalent Interactions; Thermodynamics; Titration / Volumetric Analysis
*  History
 Created:
Last Updated:		 3/16/2006
3/31/2006
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