Abstract
The organic chemistry of life is, to a great extent, the chemistry of the carbonyl group, and it is important that bioscience students should appreciate the physical effects that determine this chemistry. An experiment is described that uses attenuated total reflectance–Fourier transform infrared (ATR–FTIR) spectroscopy to teach first-year undergraduate bioscience students the significance of electronic effects in carbonyl structure and reactivity. Students first predict and then measure the carbonyl stretching frequencies of a set of compounds in a process designed to emphasize resonance and hydrogen bonding effects, both of which are frequently overlooked by inexperienced students in favor of inductive effects. Students then use their enhanced understanding of electronic effects to rationalize the reactivities of different types of carbonyl compounds to nucleophilic attack, which is an important theme in biological chemistry.
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