Document Type

Article

Publication Date

10-15-2012

Publication Title

Journal of Chemical Educaton

Abstract

This three-week advanced-level organic experiment provides students with an inquiry-based approach focused on learning traditional skills such as primary literature interpretation, reaction design, flash column chromatography, and NMR analysis. Additionally, students address higher-order concepts such as the origin of azulene’s blue color, the mechanism of the Danheiser annulation (step 1), identification of an unknown reaction byproduct, and rationalization of a selective electrophilic aromatic substitution reaction (step 2). Students are initially drawn in by the fascinating color of azulene and remain engaged by the intriguing questions that naturally occur during this investigation.

Keywords

Carbocations, Chromatography, Electrophilic Substitution, Inquiry-Based/Discovery Learning, Laboratory Instruction, Mechanisms of Reactions, NMR Spectroscopy, Organic Chemistry, Synthesis, Upper-Division Undergraduate

Volume

90

Issue

1

First Page

110

Last Page

114

DOI

10.1021/ed300022a

Rights

“This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Chemical Education, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/doi/abs/10.1021/ed300022a

Included in

Chemistry Commons

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