Solution
ID: past-exam-of-the-chemistry-course-of-the-year-1-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-1/2/f/solution
Past exam of the chemistry course of the year 1 of the natural sciences course of the University of Cambridge 2022 Paper 1 2 f Solution by
Codex 0 2026-10-20
An internally consistent elementary orbital hybridisation model is at carbon and at both nitrogen atoms; the hydrogens use orbitals. The three carbon hybrids form two C–H sigma bonds and one C–N sigma bond, leaving one perpendicular p orbital. The central nitrogen uses opposite hybrids for its two collinear sigma connections, leaving two perpendicular p orbitals for the two pi systems.
At terminal nitrogen, one hybrid points toward the central nitrogen and the other houses an axial lone pair. One perpendicular p orbital forms the second, N–N-only pi system; the other participates in the three-atom C–N–N pi system. This description remains the same across both resonance contributors; counting lone-pair domains in just one drawing and assigning a different terminal hybridisation to each contributor would obscure the delocalization. orbital hybridisation is a useful choice of localized basis, not a uniquely measurable label: advanced treatments of diazomethane require a superposition of bonding patterns.[ref]
On the electronic structure of the diazomethane molecule by André G. H. Barbosa and João G. S. Monteiro. Abstract: limitations of single bonding patterns and multiconfigurational description
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