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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 11 Issue 6 (2006) pp 406-407

Selective Reduction of Hindered Chiral Ketones. Analysis of Diastereoisomeric Products by Gas Chromatography and Polarimetry

M. Elisa S. Serra, Dina Murtinho, J. Seixas de Melo*

Chemistry Department, University of Coimbra, P3004-535 Coimbra,
Received January 21, 2006. Accepted June 22, 2006.

Published online: 18 October 2006

Abstract. The reduction of hindered chiral ketones with sodium borohydride can be analyzed by GC and polarimetry and has been revealed to be a straightforward laboratory experiment for undergraduate students to obtain contact with stereoselective reactions. The characteristic feature of this reaction, consisting in the formation of two diastereomers, is the possibility of determining the percentage of each isomer formed by GC analysis and by polarimetry using the values of the specific rotation of the mixture and the specific rotations of the pure isomers.

Key Words: Laboratories and Demonstrations; organic chemistry, chirality; optical activity, stereochemistry, gas chromatography

(*) Corresponding author. (E-mail:

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Issue date: December 1, 2006

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