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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > April  >
In the Laboratory
Epoxide Chemistry: Guided Inquiry Experiment Emphasizing Structure Determination and Mechanism
H. G. Krishnamurty, Niveta Jain, and Kiran Samby
Department of Chemistry, University of Delhi, Delhi-110007, India
Cover
April 2000
Vol. 77 No. 4
p. 511
Abstract
This paper presents an operationally simple three-step synthesis of an a-hydroxy acid based on epoxide chemistry. The focus of the experiment is on the preparation of the chalcone epoxide and its reaction with hot alcoholic alkali. The experiment leads to an unpredicted reaction product. Its structure is established as 2-benzyl-2-phenylglycollic acid by chemical and spectroscopic analysis. The hydroxyacid is a good example to bring home an important NMR principle: the nonequivalence of hydrogens adjacent to a stereogenic center. The formation of the alpha-hydroxy acid is a mechanistic puzzle. A stepwise mechanism can be developed applying lecture-based organic chemistry concepts. On the other hand, acid-catalyzed (H2SO4, BF3) reaction of the chalcone epoxide gives benzoylphenylacetaldehyde. The exercise can be used as a multistep organic chemistry experiment. It also gives students a research-type experience.
Supplement
Detailed experimental procedures for the periodic acid cleavage of the compound of interest and the acid-catalyzed rearrangement are included.
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*  Citation
 Krishnamurty, H. G.; Jain, Niveta; Samby, Kiran. J. Chem. Educ. 2000 77 511.
*  Keywords
 Chemical Education Research; Laboratory Instruction; Problem-Based Learning
*  History
 Created:
Last Updated:		 March 2, 2000
August 31, 2005
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