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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > February  >
In the Laboratory
4-Dimethylaminopyridine or Acid-Catalyzed Syntheses of Esters: A Comparison
Annemieke W. C. van den Berg and Ulf Hanefeld
Gebouw voor Scheikunde, Technische Universiteit Delft, 2628 BL Delft, The Netherlands
Cover
February 2006
Vol. 83 No. 2
p. 292
Abstract
The synthesis of esters is an essential part of first- and second-year organic chemistry laboratory classes. To highlight the differences between two standard approaches towards esters, a set of experiments was developed. With these experiments the students can compare the acid-catalyzed ester synthesis and the 4-dimethylaminopyridine-catalyzed (DMAP) reaction. As starting material the Diels–Alder adduct of anthracene and maleic anhydride was utilized, a material often synthesized in first-year organic chemistry classes. The two different products of the esterifications, the cis-diester from the acid-catalyzed reaction and the cis-monoester from the DMAP-catalyzed reaction, were purified and fully characterized (TLC, mp, IR, MS, and NMR). Based on the outcome of the experiments the students discuss the different reaction mechanisms and reason why different products are formed. Moreover, topics such as atom economy and catalysis can be introduced to the students.
Supplement
Detailed instructions for the students, notes for the instructor, and NMR and MS spectra are available.
*  Contents JCE2006p0292W.doc (Microsoft Word)
*  Download
JCE2006p0292W.pdf

JCE2006p0292W.zip
More Information
*  Citation
 van den Berg, Annemieke W. C.; Hanefeld, Ulf. J. Chem. Educ. 2006 83 292.
*  Keywords
 Acids / Bases; Catalysis; Chromatography; Esters; First-Year Undergraduate / General; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; Mass Spectrometry; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Synthesis
*  History
 Created:
Last Updated:		 1/5/2006
1/5/2006
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