This work describes a sequence of new experiments developed and used in teaching our undergraduate organic chemistry course. These experiments were selected based on the chemistry commonly used to access various organic functional materials namely: (1) Electrophilic aromatic substitution reactions and (2) Wittig reactions. Both reactions could yield visibly interesting and exciting products when highly conjugated starting materials were employed. By incorporating research with teaching in the organic lab students gained a sense of excitement through preparing and discovering new compounds as well as through collaborative learning. The reaction of activated aromatic compounds with tetracyanoethylene for instance introduced the tricyanovinyl group, a rather strong electron withdrawing group. The resulting products are highly colored, shiny metallic crystalline solids which showed solvatochromism in solution. Wittig reactions using dialdehydes result in highly conjugated fluorescent materials. Examples of simple room temperature experiments, which can be done in less than three hours, will be presented.

Design of new experiments for the organic chemistry laboratory

244th National Meeting (2012)

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