Introducing Environmentally Benign Synthesis into the Introductory Organic Lab

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 6 Issue 1 (2001) pp 25-27

Introducing Environmentally Benign Synthesis into the Introductory Organic Lab—A Greener Friedel–Crafts Acylation

Larry G. French,* Samuel S. Stradling, Martha Dudley, Dan DeBottis, and Keely Parisian

Department of Chemistry, St. Lawrence University, Canton, NY 13617
Received September 5, 2000. Accepted October 19, 2000

Published online: 29 December 2000

Abstract. An example of a more environmentally benign Friedel–Crafts acylation reaction constitutes the first step of a two step synthesis of p-anisic acid. The greener Friedel–Crafts acylation involves reaction, on acidic alumina in the absence of solvent, of anisole with a mixed anhydride derived from acetic acid and trifluoroacetic anhydride. The acylated anisole is then oxidized, employing the haloform reaction to produce p-anisic acid. Students identify the anisic acid isomer obtained through spectral analysis and/or melting-point determination and then infer the regioselectivity of the initial acylation. The experiment offers opportunities for instruction in the tenets of green chemistry and reinforcement of the theory of electrophilic aromatic substitution presented in lecture.

Key Words: Laboratories and Demonstrations; organic chemistry; Friedel-Crafts

(*) Corresponding author. (E-mail: lfrench@stlawu.edu)

Article in PDF format (131 KB) HTML format

Supporting Materials:

The student laboratory handout is available as 610022lfs1.pdf (157 KB)10.1007/ s00897000451b