The textbook argument for the stereoselective outcome of the reduction of camphor typically hinges on the definition of an arbitrary “exo” and “endo” approach, often defined in their relative distance from the one-carbon bridgehead and di-carbon bridgehead (1). As such, it may be helpful to look at the position of the LUMO on camphor (Figure 3), as it would indicate how the approach from the top-face is sterically hindered, and help connect the concept of orbitals with reactivity and bonding, an important intersection for problem-solving within chemistry. Without the additional mathematical and physical context, such topics may be better understood using 3D visualisation tools. (2,3,4) Software programs for calculation and visualisation of orbitals are becoming more common and accessible, so their potential for use as aids in the understanding of orbitals, bonding and reactivity has significantly grown.
An accessible poster & website were developed, for assistance with undergraduate students in understanding the stereoselectivity of the reduction of camphor. Freely available programs such as Avogadro, ORCA and VMD were utilised, generating an accurate depiction of camphor. This entailed optimised geometry and visible orbitals, showing the obstruction to the top face of its lowest-energy unoccupied molecular orbital (LUMO). The website was made viewable on both mobile and desktop, with straightforward language to clarify the key takeaways to the target audiences of undergraduate chemistry students. The simple format and wording make a difficult and complex topic such as orbitals easily understood by this target audience, allowing for the integration of problem-solving skills with chemical bonding and reactivity, a link not typically made in the textbook approach to this reaction.