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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

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,
Received April 28, 2016. Accepted June 14, 2016.

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:

Article in PDF format (162 KB) HTML format

Supporting Materials:

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).

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