Synthesis of Jasminaldehyde by a Crossed Aldol Condensation: An Experiment for Undergraduate Organic Chemistry Students

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 20 (2015) pp 314-320

Synthesis of Jasminaldehyde by a Crossed Aldol Condensation: An Experiment for Undergraduate Organic Chemistry Students

Steven Brettler, Nicholas Van Zee and Veljko Dragojlovic*

Wilkes Honors College of Florida Atlantic University, 5353 Parkside Drive, Jupiter, FL 33458, vdragojl@fau.edu
Received August 14, 2015. Accepted September 16, 2015.

Published: 18 November 2015

Abstract. Common undergraduate experiments investigating the crossed aldol condensation include reaction of a ketone and an aldehyde. With the active participation of undergraduate students, we have developed an undergraduate exercise involving synthesis of jasminaldehyde by a mixed aldol condensation of two aldehydes – benzaldehyde and heptanal. The optimal procedure involves a reaction of heptanal with a three-fold excess of benzaldehyde in ethanol-water solvent with sodium hydroxide as the base. Separation of jasminaldehyde from the excess benzaldehyde was a problem, and we found that it was best to allow excess benzaldehyde to react with sodium hydroxide in a Cannizzaro reaction to give water-soluble products.

Key Words: Laboratories and Demonstrations; organic chemistry, organic synthesis, aldol condensation, crossed aldol condensation, mixed aldol condensation, active learning, jasminaldehyde.

(*) Corresponding author. (E-mail: vdragojl@fau.edu )

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Supporting Materials:

Notes for the instructor, spectroscopic data, and a student handout are available as supplemental materials. (818 KB)