Solution

ID: past-exam-of-the-chemistry-course-of-the-year-1-of-the-natural-sciences-course-of-the-university-of-cambridge/2025/2/c/iii/solution

On carbon protonation, the C–N bond length increases and the N–N bond length decreases. Forming the fourth C sigma bond changes the carbon from approximately planar to tetrahedral , removing its effective C–N pi bonding. The product is described by : C–N becomes predominantly single and N–N predominantly triple. The resonance of the unprotonated species makes its actual bond orders intermediate rather than exact integers.

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