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Question

Select the correct statement about this compound.


A
All three C - N bond length are same.
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B
C1N and C3N bonds length are same but shorter than C5N bonds length.
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C
C1N and C5N bonds length are same but longer than C3N bond length.
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D
C1N and C3N bonds length are different but both are longer than C5N bond length.
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Solution

The correct option is C C1N and C5N bonds length are same but longer than C3N bond length.
In the given compound, due to larger size of bromine atom it create a steric crowding for ortho position NO2 groups. Due to this steric hindrance the ortho positioned NO2 will get out of benzene plane. Since it is no longer in the plane it wont participitate in resonance of the molecule. But para positioned NO2 does not fell any steric effect from Br so it will involve in resonance of the molecule. Therefore CNin para position acquire double bond character, hence the bond length is shorter than the CN bond length in ortho position

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