A Solvent-free Oxidation of 1-Pentanol to Pentanoic Acid for the Undergraduate Organic Laboratory

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 9 Issue 1 (2004) pp 30-31

A Solvent-free Oxidation of 1-Pentanol to Pentanoic Acid for the Undergraduate Organic Laboratory

Jaclyn A. Barrett, John J. Esteb,* Geoffrey C. Hoops, and Jeremy M. Richter

Butler University, Clowes Department of Chemistry, 4600 Sunset Avenue, Indianapolis, Indiana 46208, jesteb@butler.edu.
Received August 30, 2003. Accepted September 19, 2003.

Published online: 9 January 2004

Abstract. Herein we present an oxidation experiment for a first-year organic chemistry class. This oxidation utilizes a solid mixture of CuSO₄^·5 H₂O and KMnO₄ prepared by the students using a mortar and pestle. The oxidation takes place under solvent-free conditions and a good yield is obtained for the reaction. This experiment provides for the simple oxidation of a primary alcohol to a carboxylic acid using a relatively nontoxic oxidizing agent under solvent-free conditions. Furthermore, students are able to utilize acid–base extraction techniques for purification of the final product.

Key Words: Laboratories and Demonstrations; organic chemistry; organic synthesis; laboratory instruction; oxidation reactions; solvent-free

(*) Corresponding author. (E-mail: jesteb@butler.edu)

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Supporting Materials:

A laboratory handout out for students is available (26 KB zip file).