Past exam of the chemistry course of the year 1 of the natural sciences course of the University of Cambridge / 2025 / 2 / c / i / Solution

One consistent localized orbital hybridization description uses the Lewis structuresFor methyldiazonium, take C as $s{p}^3$ and both N atoms as $sp$. For diazomethane, the double-bond resonance contributor suggests C as $s{p}^2$, central N as $sp$, and terminal N as $s{p}^2$. The central N uses two opposite $sp$ hybrids for the linear C–N–N sigma bond framework. In the localized double-bond picture, terminal N uses one $s{p}^2$ hybrid for its sigma bond, two for lone pairs, and its remaining p atomic orbital for a pi bond.

These labels specify an approximate bonding construction, not uniquely measurable atomic properties. An alternative representation takes terminal N as $sp$, with one $sp$ lone pair and one p lone pair; the latter can participate in the delocalized C–N–N $\pi$ system. It describes the same resonance more explicitly. Neither construction requires an unpaired electron or a bent central N.