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Hydrocarbons question

2021 · 20 Jul · Shift 2 · Q11
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Hydrocarbons question

2021 · 20 Jul · Shift 2 · Q11

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Benzene on nitration gives nitrobenzene in presence of HNO3HNO_3HNO3​ and H2SO4H_2SO_4H2​SO4​ mixture, where :
  1. A
    both H2SO4H_2SO_4H2​SO4​ and HNO3HNO_3HNO3​ act as a bases
  2. B
    HNO3HNO_3HNO3​ acts as an acid and H2SO4H_2SO_4H2​SO4​ acts as a base
  3. C
    both H2SO4H_2SO_4H2​SO4​ and HNO3HNO_3HNO3​ act as an acids
  4. D
    HNO3HNO_3HNO3​ acts as a base and H2SO4H_2SO_4H2​SO4​ acts as an acid
View written solutionFree

Correct answer: D

  1. Identify the role of the acid mixture in nitration

    Benzene nitration occurs using the nitrating mixture of concentrated HNO3HNO_3HNO3​ and concentrated H2SO4H_2SO_4H2​SO4​.

    The actual electrophile that attacks benzene is the nitronium ion, NO2+NO_2^+NO2+​.

  2. Formation of the electrophile

    The first step is protonation of nitric acid by sulfuric acid:

    HNO3+H2SO4→H2NO3++HSO4−HNO_3 + H_2SO_4 \rightarrow H_2NO_3^+ + HSO_4^-HNO3​+H2​SO4​→H2​NO3+​+HSO4−​

    Here:

    • H2SO4H_2SO_4H2​SO4​ donates a proton, so it acts as an acid.
    • HNO3HNO_3HNO3​ accepts a proton, so it acts as a base.
  3. Generation of nitronium ion

    The protonated nitric acid then loses water:

    H2NO3+→NO2++H2OH_2NO_3^+ \rightarrow NO_2^+ + H_2OH2​NO3+​→NO2+​+H2​O

    Thus, the nitrating species is formed.

  4. Conclusion about acid-base roles

    In the mixed acid system:

    • H2SO4H_2SO_4H2​SO4​ acts as an acid
    • HNO3HNO_3HNO3​ acts as a base
  5. Evaluate options

    • A: both act as bases  Incorrect
    • B: HNO3HNO_3HNO3​ acid, H2SO4H_2SO_4H2​SO4​ base  Incorrect
    • C: both act as acids  Incorrect
    • D: HNO3HNO_3HNO3​ acts as a base and H2SO4H_2SO_4H2​SO4​ acts as an acid  Correct

Therefore, the correct answer is:

D\boxed{D}D​

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