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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 8 Issue 4 (2003) pp 241-243

Oxidation of an Unknown Cycloalkene, Cycloalkanol, or Cycloalkanone to a Dicarboxylic Acid: A Discovery Oriented Experiment for Organic Chemistry Students

Janne T. Nielsen,1, Robert Duarte2 and Veljko Dragojlovic1,*

1Oceanographic Center, Nova Southeastern University, 8000 North Ocean Drive, Dania, FL 33004,; and 2Department of Math, Science and Technology, Farquhar College of Arts and Sciences, Nova Southeastern University, 3301 College Avenue, Fort Lauderdale, FL 33314
Received February 13, 2003. Accepted May 3, 2003.

Published online: 10 July 2003

Abstract. Oxidative degradation is a technique commonly used in structural elucidation of organic compounds. In this laboratory exercise, each student is issued an unknown cyclic compound. The students first have to determine the functional group of the unknown compound (alcohol, ketone, or alkene). Next, the students have to perform an oxidative degradation of the unknown compound to the corresponding dicarboxylic acid. They identify the isolated dicarboxylic acid either from its melting point or IR spectrum. Finally, once the students know both the original functional group and the identity of the dicarboxylic acid that resulted from the oxidation of their unknown, they are expected to elucidate the structure of the original unknown compound. This experiment takes two three-hour laboratory sessions. It introduces chemical degradation techniques to students and provides them with an introduction to retrosynthetic thinking. The experiment is designed as a discovery-based laboratory exercise for an introductory organic chemistry course. The article and supplementary material include background information on the oxidation methods used in the exercise.

Key Words:  Laboratories and Demonstrations; organic chemistry; organic synthesis; oxidation; ruthenium tetroxide; potassium permanganate

(*) Corresponding author. (E-mail:

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A Handout to Students and Notes to Instructors are available in the one compressed Zip file (178 KB) (

Issue date: August 1, 2003

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