The Chemical Educator
ISSN: 1430-4171 (electronic version)
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, email@example.com
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: firstname.lastname@example.org)
Notes for the instructor, spectroscopic data, and a student handout are available as supplemental materials. (818 KB)