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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > June  >
In the Laboratory
The Microscale Laboratory
Iodolactonization of 4-Pentenoic Acid
R. David Crouch, Alexander Tucker-Schwartz, and Kathryn Barker
Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896
Cover
June 2006
Vol. 83 No. 6
p. 921
Abstract
An experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization is described. In this lab activity, the alkenoic acid is treated with I2 prepared in situ, forming an iodonium ion that undergoes intramolecular nucleophilic attack to produce 5-iodo-γ-valerolactone. Students use the infrared spectrum to determine which functional groups are present in the product and their understanding of the nature of the reactants to determine that product formation occurs through attack of the carboxylic acid's oxygen on the iodonium ion intermediate. The NMR spectrum of the product establishes that nucleophilic attack occurs in accordance with Markovnikov's rule.
Supplement
Instructions for the students and notes for the instructor are available.
*  Contents JCE2006p0921W.doc (Microsoft Word)
*  Download
JCE2006p0921W.pdf

JCE2006p0921W.zip
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*  Citation
 Crouch, R. David; Tucker-Schwartz, Alexander; Barker, Kathryn. J. Chem. Educ. 2006 83 921.
*  Keywords
 Alkenes; Carboxylic Acids; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; Mechanisms of Reactions; NMR Spectroscopy; Organic Chemistry; Problem Solving / Decision Making; Reactions; Second-Year Undergraduate; Synthesis
*  History
 Created:
Last Updated:		 4/24/2006
5/3/2006
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