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Compounds Containing Nitrogen question

2019 · 12 Apr · Shift 2 · Q2
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Compounds Containing Nitrogen question

2019 · 12 Apr · Shift 2 · Q2

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Benzene diazonium chloride on reaction with aniline in the presence of dilute hydrochloric acid gives :
  1. A
    JEE Main 2019 (Online) 12th April Evening Slot Chemistry - Compounds Containing Nitrogen Question 179 English Option 1
  2. B
    JEE Main 2019 (Online) 12th April Evening Slot Chemistry - Compounds Containing Nitrogen Question 179 English Option 2
  3. C
    JEE Main 2019 (Online) 12th April Evening Slot Chemistry - Compounds Containing Nitrogen Question 179 English Option 3
  4. D
    JEE Main 2019 (Online) 12th April Evening Slot Chemistry - Compounds Containing Nitrogen Question 179 English Option 4
View written solutionFree

Correct answer: A

  1. Identify the reaction type

Benzene diazonium chloride reacts with aniline in mildly acidic medium to give an azo coupling reaction.

The diazonium salt acts as the electrophile, and aniline (or its activated aromatic ring) acts as the coupling component.


  1. Nature of coupling with aniline

Aniline has an electron-donating group, −NH2-NH_2−NH2​, which activates the benzene ring and directs incoming electrophile to the ortho and para positions.

During azo coupling, the electrophile is the benzenediazonium ion:

C6H5N2+C_6H_5N_2^+C6​H5​N2+​

So coupling occurs mainly at the para position of aniline because:

  • para product is more stable,
  • less steric hindrance than ortho product.

  1. Product formed

Thus the product is:

C6H5−N=N−C6H4−NH2C_6H_5-N=N-C_6H_4-NH_2C6​H5​−N=N−C6​H4​−NH2​

with −NH2-NH_2−NH2​ at the para position relative to the azo group.

This compound is called p-aminoazobenzene (or aniline yellow).


  1. Conclusion

So, benzene diazonium chloride + aniline in dilute HCl gives p-aminoazobenzene as the major product.

Since the options are not visible, we identify the correct option as the one representing para-aminoazobenzene.


  1. Comparison with stored answer

The stored correct answer is A. Since the standard product of this reaction is p-aminoazobenzene, I agree provided option A corresponds to p-aminoazobenzene.

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