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Compounds Containing Nitrogen question

2016 · 10 Apr · Shift 1 · Q2
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Compounds Containing Nitrogen question

2016 · 10 Apr · Shift 1 · Q2

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
The “N” which does not contribute to the basicity for the compound is : JEE Main 2016 (Online) 10th April Morning Slot Chemistry - Compounds Containing Nitrogen Question 201 English
  1. A
    N 7
  2. B
    N 9
  3. C
    N 1
  4. D
    N 3
View written solutionFree

Correct answer: B

  1. Identify the structure and the labeled nitrogens

    The question refers to a fused heterocyclic system with nitrogens labeled N1,N3,N7,N_1, N_3, N_7,N1​,N3​,N7​, and N9N_9N9​ (as in purine-type numbering).

    We must find which nitrogen does not contribute to basicity.

  2. Principle of basicity in heterocycles

    A nitrogen contributes to basicity if its lone pair is available for protonation.

    • Pyridine-like nitrogen: lone pair is outside the aromatic sextet, so it is available for protonation  basic.
    • Pyrrole-like nitrogen: lone pair is part of the aromatic sextet, so it is not available for protonation  does not contribute to basicity.
  3. Examine the labeled nitrogens

    In the purine framework:

    • N1N_1N1​ and N3N_3N3​ are pyridine-like nitrogens. Their lone pairs are not part of the aromatic sextet, so they can accept a proton.
    • N7N_7N7​ is also pyridine-like, so its lone pair is available for protonation.
    • N9N_9N9​ is pyrrole-like. Its lone pair participates in maintaining aromaticity of the imidazole-like ring.

    Therefore, protonating N9N_9N9​ would disrupt the aromatic electron delocalization, so this lone pair is not available for basic behavior.

  4. Conclusion

    The nitrogen that does not contribute to basicity is:

    N9N_9N9​

  5. Option check

    • A: N7N_7N7​  contributes to basicity
    • B: N9N_9N9​  does not contribute to basicity
    • C: N1N_1N1​  contributes to basicity
    • D: N3N_3N3​  contributes to basicity

    Hence, the correct option is B.

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