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Compounds Containing Nitrogen question

2021 · 24 Feb · Shift 1 · Q8
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Compounds Containing Nitrogen question

2021 · 24 Feb · Shift 1 · Q8

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
In the following reaction the reason why meta-nitro product also formed is : JEE Main 2021 (Online) 24th February Morning Shift Chemistry - Compounds Containing Nitrogen Question 162 English
  1. A
    –NH2NH_2NH2​ group is highly meta-directive
  2. B
    –NO2NO_2NO2​ substitution always takes place at meta-position
  3. C
    Formation of anilinium ion
  4. D
    low temperature
View written solutionFree

Correct answer: C

  1. Identify the reaction situation

    The question refers to nitration of aniline (or a related ring containing the −NH2-NH_2−NH2​ group), where along with the expected products, a meta-nitro product is also formed.

  2. Usual directing effect of −NH2-NH_2−NH2​

    The amino group (−NH2)(-NH_2)(−NH2​) is normally a strong activating, ortho/para-directing group because its lone pair donates electron density into the benzene ring by resonance.

    So, if free aniline undergoes electrophilic substitution, we expect mainly:

    • ortho product
    • para product

    Therefore, option A is false because −NH2-NH_2−NH2​ is not meta-directing.

  3. What happens during nitration conditions?

    Nitration is carried out in a strongly acidic medium, usually with a mixture of concentrated HNO3HNO_3HNO3​ and concentrated H2SO4H_2SO_4H2​SO4​.

    In this acidic medium, the amino group gets protonated:

    C6H5NH2+H+→C6H5NH3+C_6H_5NH_2 + H^+ \rightarrow C_6H_5NH_3^+C6​H5​NH2​+H+→C6​H5​NH3+​

    This species is called the anilinium ion.

  4. Directing effect of anilinium ion

    The group −NH3+-NH_3^+−NH3+​ is electron-withdrawing and meta-directing.

    Hence, once aniline is converted into anilinium ion under nitration conditions, some substitution occurs at the meta position, which explains the formation of the meta-nitro product.

  5. Check other options

    • B: "−NO2-NO_2−NO2​ substitution always takes place at meta-position"
      False. The entering electrophile is the nitronium ion NO2+NO_2^+NO2+​, and the position of substitution depends on the group already present on the ring.

    • D: low temperature
      False. Low temperature is not the reason for meta substitution here.

  6. Conclusion

    The meta product is formed because the amino group is protonated in acidic medium to give anilinium ion, which is meta-directing.

    Therefore, the correct option is:

    C\boxed{C}C​

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