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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 16 (2011) pp 307-309

Microscale Catalytic and Chemoselective TPAP Oxidation of Geraniol

Katherine J. Koroluk, Stanislaw Skonieczny, and Andrew P. Dicks*

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6,
Received September 13, 2011. Accepted October 10, 2011.

Published: 21 November 2011

Abstract. The mild, room-temperature oxidation of a primary alcohol catalyzed by tetrapropylammonium perruthenate (TPAP) is presented for the undergraduate organic laboratory. In this experiment, geraniol is oxidized to form geranial, a liquid product that is easily characterized via IR and proton NMR spectroscopy. Both substrate and product have very distinct and pleasant odours, so their respective reactivity and formation generates class interest. Comparison between this synthesis and other alcohol oxidation procedures affords discussion of catalytic behaviour apparent in the former method. Although catalysis is favourable in terms of green chemistry, certain improvements can be made from a sustainability perspective, which is an important focal point for student discourse. The reaction also provides an opportunity to perform a reaction under dry conditions, and to investigate a detailed autocatalytic mechanism of TPAP oxidation.

Key Words: Laboratories and Demonstrations; organic chemistry; nuclear magnetic resonance; pyranoside stereochemistry

(*) Corresponding author. (E-mail:

Article in PDF format (35 KB) HTML format

Supporting Materials:

Detailed experimental notes for students and instructors (including a simple procedure for TPAP preparation) and representative product spectra are provided in the supporting materials accompanying this paper (122 KB).

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