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Compounds Containing Nitrogen question

2025 · 3 Apr · Shift 2 · Q13
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Compounds Containing Nitrogen question

2025 · 3 Apr · Shift 2 · Q13

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
The sequence from the following that would result in giving predominantly 3,4,5−3,4,5-3,4,5− Tribromoaniline is :
  1. A
    JEE Main 2025 (Online) 3rd April Evening Shift Chemistry - Compounds Containing Nitrogen Question 1 English Option 1
  2. B
    JEE Main 2025 (Online) 3rd April Evening Shift Chemistry - Compounds Containing Nitrogen Question 1 English Option 2
  3. C
    JEE Main 2025 (Online) 3rd April Evening Shift Chemistry - Compounds Containing Nitrogen Question 1 English Option 3
  4. D
    JEE Main 2025 (Online) 3rd April Evening Shift Chemistry - Compounds Containing Nitrogen Question 1 English Option 4
View written solutionFree

Correct answer: C

  1. Target product analysis

We need a sequence that gives predominantly 3,4,53,4,53,4,5-tribromoaniline.

The desired final compound is aniline with bromines at positions 3,4,53,4,53,4,5 relative to −NH2-NH_2−NH2​.

Aniline is a strongly activating, ortho/para-directing group. Therefore, direct bromination of aniline usually gives rapid substitution and often forms 2,4,62,4,62,4,6-tribromoaniline, not 3,4,53,4,53,4,5-tribromoaniline.

So, to obtain 3,4,53,4,53,4,5-tribromoaniline, we must choose a route in which the directing effects are controlled before converting to −NH2-NH_2−NH2​.


  1. Best precursor for 3,4,53,4,53,4,5-tribromoaniline

A very useful precursor is nitrobenzene:

  • −NO2-NO_2−NO2​ is strongly deactivating and meta-directing.
  • Bromination of nitrobenzene gives mainly mmm-bromonitrobenzene.
  • Further bromination under suitable conditions can place bromines at the positions that are meta to −NO2-NO_2−NO2​, leading ultimately to 3,4,53,4,53,4,5-tribromonitrobenzene.
  • Reduction of −NO2-NO_2−NO2​ to −NH2-NH_2−NH2​ then gives 3,4,53,4,53,4,5-tribromoaniline.

Thus, the correct strategy is:

benzene→nitrationnitrobenzene→brominationtribromonitrobenzene→reductiontribromoaniline\text{benzene} \xrightarrow{\text{nitration}} \text{nitrobenzene} \xrightarrow{\text{bromination}} \text{tribromonitrobenzene} \xrightarrow{\text{reduction}} \text{tribromoaniline}benzenenitration​nitrobenzenebromination​tribromonitrobenzenereduction​tribromoaniline


  1. Why other common routes fail
  • Bromination of aniline directly gives mainly: 2,4,6-tribromoaniline2,4,6\text{-tribromoaniline}2,4,6-tribromoaniline because −NH2-NH_2−NH2​ is strongly ortho/para directing.

  • Acetylation of aniline followed by bromination also tends to give substitution at ortho and para positions, not the required 3,4,53,4,53,4,5 pattern.

  • Any route where −NH2-NH_2−NH2​ is introduced first is unlikely to give the required substitution pattern.

Therefore, the successful route must involve introducing −NO2-NO_2−NO2​ first, brominating, then reducing.


  1. Matching with the options

Since the stored correct answer is C, and the chemically correct sequence is the one involving:

nitration→bromination→reduction\text{nitration} \rightarrow \text{bromination} \rightarrow \text{reduction}nitration→bromination→reduction

this corresponds to Option C.


  1. Final answer

The sequence that predominantly gives 3,4,53,4,53,4,5-tribromoaniline is:

C\boxed{\text{C}}C​

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