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Compounds Containing Nitrogen question

2022 · 28 Jun · Shift 2 · Q11
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Compounds Containing Nitrogen question

2022 · 28 Jun · Shift 2 · Q11

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
With respect to the following reaction, consider the given statements : JEE Main 2022 (Online) 28th June Evening Shift Chemistry - Compounds Containing Nitrogen Question 109 English (A) o-Nitroaniline and p-nitroaniline are the predominant products. (B) p-Nitroaniline and m-nitroaniline are the predominant products. (C) HNO3HNO_3HNO3​ acts as an acid. (D) H2SO4H_2SO_4H2​SO4​ acts as an acid. Choose the correct option.
  1. A
    (A) and (C) are correct statements.
  2. B
    (A) and (D) are correct statements.
  3. C
    (B) and (D) are correct statements.
  4. D
    (B) and (C) are correct statements.
View written solutionFree

Correct answer: C

  1. Identify the reaction conditions

    The question refers to nitration of aniline using the usual nitrating mixture: aniline+HNO3/H2SO4\text{aniline} + HNO_3/H_2SO_4aniline+HNO3​/H2​SO4​

  2. What happens to aniline in strongly acidic medium?

    Aniline is basic, so in the presence of strong acid it gets protonated: C6H5NH2+H+→C6H5NH3+C_6H_5NH_2 + H^+ \rightarrow C_6H_5NH_3^+C6​H5​NH2​+H+→C6​H5​NH3+​

    Thus, under nitrating conditions, a significant amount of aniline exists as the anilinium ion.

  3. Directing effect of the protonated amino group

    • Free −NH2-NH_2−NH2​ group is ortho/para-directing.
    • But protonated −NH3+-NH_3^+−NH3+​ group is deactivating and meta-directing.

    Therefore, in the strongly acidic nitration medium, nitration occurs predominantly at the meta position.

    However, some free aniline may still be present, giving a little para product. In standard JEE interpretation, the major products are taken as:

    • ppp-nitroaniline
    • mmm-nitroaniline

    Hence statement (B) is correct, while (A) is not.

  4. Role of HNO3HNO_3HNO3​ and H2SO4H_2SO_4H2​SO4​

    In the nitrating mixture: HNO3+H2SO4→NO2++HSO4−+H2OHNO_3 + H_2SO_4 \rightarrow NO_2^+ + HSO_4^- + H_2OHNO3​+H2​SO4​→NO2+​+HSO4−​+H2​O

    Here, H2SO4H_2SO_4H2​SO4​ being the stronger acid protonates HNO3HNO_3HNO3​, so:

    • H2SO4H_2SO_4H2​SO4​ acts as an acid
    • HNO3HNO_3HNO3​ acts as a base

    Therefore:

    • Statement (C) "HNO3HNO_3HNO3​ acts as an acid" is false
    • Statement (D) "H2SO4H_2SO_4H2​SO4​ acts as an acid" is true
  5. Evaluate the given statements

    • (A) ooo-Nitroaniline and ppp-nitroaniline are predominant products. False
    • (B) ppp-Nitroaniline and mmm-nitroaniline are predominant products. True
    • (C) HNO3HNO_3HNO3​ acts as an acid. False
    • (D) H2SO4H_2SO_4H2​SO4​ acts as an acid. True
  6. Choose the correct option

    Correct statements are (B) and (D).

    Therefore, the correct option is: C\boxed{\text{C}}C​

  7. Comparison with stored answer

    Stored correct answer = C.

    Our derived answer also = C. So they agree.

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