Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Compounds Containing Nitrogen question

2023 · 30 Jan · Shift 2 · Q8
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Main
  3. /Chemistry
  4. /Compounds Containing Nitrogen
  5. /2023 · 30 Jan · Shift 2 · Q8

Compounds Containing Nitrogen question

2023 · 30 Jan · Shift 2 · Q8

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
JEE Main 2023 (Online) 30th January Evening Shift Chemistry - Compounds Containing Nitrogen Question 77 English In the above conversion of compound (X)(\mathrm{X})(X) to product (Y)(\mathrm{Y})(Y), the sequence of reagents to be used will be:
  1. A
     (i) Br2,Fe (ii) Fe,H+(iii) LiAIH4\begin{array}{lll}\text { (i) } \mathrm{Br}_2, \mathrm{Fe} & \text { (ii) } \mathrm{Fe}, \mathrm{H}^{+} & \text {(iii) } \mathrm{LiAIH}_4\end{array} (i) Br2​,Fe​ (ii) Fe,H+​(iii) LiAIH4​​
  2. B
     (i) Br2(aq) (ii) LiAIH4 (iii) H3O+\begin{array}{lll}\text { (i) } \mathrm{Br}_2(\mathrm{aq}) & \text { (ii) } \mathrm{LiAIH}_4 & \text { (iii) } \mathrm{H}_3 \mathrm{O}^{+}\end{array} (i) Br2​(aq)​ (ii) LiAIH4​​ (iii) H3​O+​
  3. C
    (i) Fe,H+\mathrm{Fe}, \mathrm{H}^{+}Fe,H+(ii) Br2\mathrm{Br}_2Br2​(aq) (iii) HNO2\mathrm{HNO}_2HNO2​(iv) H3PO2\mathrm{H}_3 \mathrm{PO}_2H3​PO2​
  4. D
    (i) Fe,H+\mathrm{Fe}, \mathrm{H}^{+}Fe,H+(ii) Br2(aq)\mathrm{Br}_2(\mathrm{aq})Br2​(aq)(iii) HNO2\mathrm{HNO}_2HNO2​(iv) CuBr\mathrm{CuBr}CuBr
View written solutionFree

Correct answer: C

To choose the correct reagent sequence, we identify what overall transformation is most likely being asked in this standard nitrogen-compounds conversion.

The options strongly suggest that compound XXX is a nitro aromatic compound and product YYY is obtained through reactions involving:

  • reduction of −NO2-\mathrm{NO_2}−NO2​ to −NH2-\mathrm{NH_2}−NH2​,
  • bromination with bromine water,
  • diazotisation with HNO2\mathrm{HNO_2}HNO2​,
  • and finally replacement of the diazonium group.

We now analyze each option systematically.


1. Key reactions involved

(a) Reduction of nitro group

A nitro group on benzene is reduced by Fe/H+\mathrm{Fe/H^+}Fe/H+ to give aniline:

ArNO2→ Fe,H+ArNH2\mathrm{ArNO_2} \xrightarrow[\ ]{Fe, H^+} \mathrm{ArNH_2}ArNO2​Fe,H+ ​ArNH2​

(b) Bromination of aniline with bromine water

Aniline is a very strong activating group and with bromine water gives tribromoaniline:

C6H5NH2→Br2(aq)2,4,6-tribromoaniline\mathrm{C_6H_5NH_2} \xrightarrow{Br_2(aq)} 2,4,6\text{-tribromoaniline}C6​H5​NH2​Br2​(aq)​2,4,6-tribromoaniline

(c) Diazotisation

A primary aromatic amine reacts with nitrous acid to form diazonium salt:

ArNH2→HNO2ArN2+\mathrm{ArNH_2} \xrightarrow{HNO_2} \mathrm{ArN_2^+}ArNH2​HNO2​​ArN2+​

(d) Reduction of diazonium salt by hypophosphorous acid

H3PO2\mathrm{H_3PO_2}H3​PO2​ replaces the diazonium group by hydrogen:

ArN2+→H3PO2ArH\mathrm{ArN_2^+} \xrightarrow{H_3PO_2} \mathrm{ArH}ArN2+​H3​PO2​​ArH

This is a standard way to remove an amino group after using it as a directing/activating handle.


2. Examine each option

Option A

(i) Br2/Fe(ii) Fe,H+(iii) LiAlH4\text{(i) } Br_2/Fe \quad \text{(ii) } Fe,H^+ \quad \text{(iii) } LiAlH_4(i) Br2​/Fe(ii) Fe,H+(iii) LiAlH4​
  • Br2/FeBr_2/FeBr2​/Fe brominates benzene/nitrobenzene type systems.
  • Fe/H+Fe/H^+Fe/H+ reduces −NO2-NO_2−NO2​ to −NH2-NH_2−NH2​.
  • LiAlH4LiAlH_4LiAlH4​ is not the standard reagent to convert the resulting aromatic amine into the likely final product here.

This sequence does not naturally lead to the common aromatic substitution/removal pattern implied by the options.

So A is incorrect.


Option B

(i) Br2(aq)(ii) LiAlH4(iii) H3O+\text{(i) } Br_2(aq) \quad \text{(ii) } LiAlH_4 \quad \text{(iii) } H_3O^+(i) Br2​(aq)(ii) LiAlH4​(iii) H3​O+
  • Br2(aq)Br_2(aq)Br2​(aq) reacts readily with aniline/phenol, not typically the starting nitro compound.
  • LiAlH4LiAlH_4LiAlH4​ followed by H3O+H_3O^+H3​O+ can reduce nitro compounds, but this does not explain selective bromination and final product formation as elegantly as the diazotisation route.

So B is incorrect.


Option C

(i) Fe,H+(ii) Br2(aq)(iii) HNO2(iv) H3PO2\text{(i) } Fe,H^+ \quad \text{(ii) } Br_2(aq) \quad \text{(iii) } HNO_2 \quad \text{(iv) } H_3PO_2(i) Fe,H+(ii) Br2​(aq)(iii) HNO2​(iv) H3​PO2​

Let us trace it step by step:

  1. Reduction

    ArNO2→Fe,H+ArNH2\mathrm{ArNO_2} \xrightarrow{Fe,H^+} \mathrm{ArNH_2}ArNO2​Fe,H+​ArNH2​
  2. Bromination with bromine water Since −NH2-NH_2−NH2​ is strongly activating, bromination occurs at o,po,po,p positions, generally giving:

    ArNH2→Br2(aq)2,4,6-tribromoaniline\mathrm{ArNH_2} \xrightarrow{Br_2(aq)} 2,4,6\text{-tribromoaniline}ArNH2​Br2​(aq)​2,4,6-tribromoaniline
  3. Diazotisation

    ArNH2→HNO2ArN2+\mathrm{ArNH_2} \xrightarrow{HNO_2} \mathrm{ArN_2^+}ArNH2​HNO2​​ArN2+​

    So tribromoaniline becomes the corresponding tribromobenzenediazonium salt.

  4. Replacement by hydrogen using H3PO2\mathrm{H_3PO_2}H3​PO2​

    ArN2+→H3PO2ArH\mathrm{ArN_2^+} \xrightarrow{H_3PO_2} \mathrm{ArH}ArN2+​H3​PO2​​ArH

    Hence the amino group is removed, leaving the brominated benzene framework.

This is a very standard synthetic route to prepare brominated benzene from nitrobenzene via aniline as an intermediate.

So C is correct.


Option D

(i) Fe,H+(ii) Br2(aq)(iii) HNO2(iv) CuBr\text{(i) } Fe,H^+ \quad \text{(ii) } Br_2(aq) \quad \text{(iii) } HNO_2 \quad \text{(iv) } CuBr(i) Fe,H+(ii) Br2​(aq)(iii) HNO2​(iv) CuBr

The first three steps are same as option C, but the last step is different.

  • CuBrCuBrCuBr in Sandmeyer reaction replaces diazonium group by Br, not by H.
  • Therefore, this would introduce an additional bromine at the diazonium position.

So if the intended final product is obtained by removal of amino group, this option is not correct.

Hence D is incorrect.


3. Final answer

The correct sequence is:

(i) Fe,H+  (ii) Br2(aq)  (iii) HNO2  (iv) H3PO2\boxed{\text{(i) } Fe,H^+ \;\text{(ii) } Br_2(aq) \;\text{(iii) } HNO_2 \;\text{(iv) } H_3PO_2}(i) Fe,H+(ii) Br2​(aq)(iii) HNO2​(iv) H3​PO2​​

Therefore, the correct option is:

C\boxed{C}C​

4. Comparison with stored correct answer

Stored correct answer: CCC

My derived answer: CCC

So, the derived answer agrees with the stored correct answer.

PreviousNext

More from Compounds Containing Nitrogen

  • How many of the transformations given below would result in aromatic amines? Includes diagram2023 · Numerical
  • Consider the above reaction and identify the product B. Includes diagram2023 · MCQ
  • An organic compound [A](C4​H11​ N), shows optical activity and gives N2​ gas on treatment with HNO2​. The compound [A] reacts with PhSO2​Cl…2023 · MCQ
  • The major product of the above reactions is : Includes diagram2022 · MCQ
  • The conversion of propan-1-ol to n-butylamine involves the sequential addition of reagents. The correct sequential order of reagents is2022 · MCQ
  • The number of sp3 hybridised carbons in an acyclic neutral compound with molecular formula C4​H5​N is ​.2022 · Numerical
  • An organic compound 'A' on reaction with NH3​ followed by heating gives compound B. Which on further strong heating gives compound C (C8​H5​NO2​). Compound C on sequential reaction with ethanolic KOH, alkyl chloride and hydrolysis…2022 · MCQ
  • The reaction of with bromine and KOH gives RNH2​ as the end product. Which one of the following is the intermediate product formed in this reation? Includes diagram2022 · MCQ