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Q.
Arrange the following compounds in increasing order of
length of their $C - N$ bond.
Organic Chemistry – Some Basic Principles and Techniques
Solution:
The bond order of $C - N$ bond is $2$ in III, shortest, $1$ in II, longest bond. There is greater extent of delocalisation of nitrogen lone pair in IV because it brings negative charge on oxygen than in I where negative charge moves on carbon.
Hence, $C - N$ bond acquire greater partial double bond character in IV than in I. This results in greater shortening of $C-N$ bond length in IV than in I, although I has more resonating structures.
