Q.
Arrange the following compounds in increasing order of
length of their C−N bond.
500
188
Organic Chemistry – Some Basic Principles and Techniques
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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.
