Iodolactonization of 4-Pentenoic Acid

R. David Crouch , Alexander Tucker-Schwartz and Kathryn Barker
Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896
J. Chem. Educ., 2006, 83 (6), p 921
DOI: 10.1021/ed083p921
Publication Date (Web): June 1, 2006
History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Alkenes
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  • Received: August 03, 2009

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