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Imdadul Haque posted an Question

January 05, 2021 • 13:27 pm

30 points

IIT JAM
Chemistry (CY)

81. arrange the following compound, in order of c-n bond length. no me me me me me me (bo oom (d) met (a) me no, no2 no2

81. Arrange the following compound, in order of C-N bond length. NO Me Me Me Me Me Me (BO oOM (D) MeT (A) Me NO, NO2 NO2

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Suman Kumar

D> C>A>B D has ortho effect so there is no resonance But B has 1 methyl group at para position which shows hyperconjugation adding extra stability
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Dinesh khalmaniya 1 Best Answer

D>C>A>B Explanation- here in D, there is SIR effect so NO2 group doesn't show resonance with ring due to steric hindrance and have purely single bond. so D has higher bond length Between C-N. In case of B there is also ortho effect so resonance is less as compared to D. so bond length with be slightly less than D. in case of A and B, B has Me group at para position. it show +H effect so A>B.
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Priyanshu kumar

D>C>A>B. bond length of purely single bond > partial double bond>purely double bond. In compound D due to SIR effect there is no resonance..so there is purely C-N single bond...Hence D has highest C-N bond length. In C also due to ortho methyl group...the resonance is somehow diminishes so it has less SIR effect than D and hence less bond length than D. In between A and B there is more extent of resonance in case of B than A...so double bond character in C-N bond length increases and single bond character decreases.
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Yes Sir 👍
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