The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 21
(2016) pp 136-138
Synthesis and Bioassay of 2-Naphthylmethanol, a Synthetic Trail Pheromone of Termites
Patricia M. Smiley† and William H. Miles*,‡
†Southern Lehigh High School, Center Valley, PA 18034; ‡Department of Chemistry, Lafayette College, Easton, PA 18042, email@example.com
Published: 15 July 2016
Abstract. The one-step sodium borohydridereduction of 2-naphthaldehyde to 2-naphthylmethanol is an excellent vehicle for introducing oxidations and reductions to organic chemistry students as well as AP Chemistry students. The experiment described herein also demonstrates the effectiveness of a synthetic trail pheromone for the eastern subterranean termite, Reticulitermes flavipes. As described in the patent literature, the alcohol product 2-naphthylmethanol increases the utility of poisoned baits used to trap termites. A simple but appealing bioassay is described that illustrates this trail-following behavior. The experiment explores many facets of organic chemistry, including pheromones, the stereochemistry of biological receptors, structure determination, and patent literature.
Key Words: Laboratories and Demonstrations; organic chemistry; pheromone; reduction; sodium borohydride; IR; NMR; patents
(*) Corresponding author. (E-mail: firstname.lastname@example.org)
A copy of the student handout with the full experimental details and instructor notes, as well as the IR and 1H NMR spectra for both 2-naphthaldehyde and 2-naphthylmethanol are provided. (591 KB).