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 · Shift 2 · Q17
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 Advanced
  3. /Chemistry
  4. /Compounds Containing Nitrogen
  5. /2023 · Shift 2 · Q17

Compounds Containing Nitrogen question

2023 · Shift 2 · Q17

JEE AdvancedChemistryCompounds Containing NitrogenNumerical+3 / −1
A trinitro compound, 1,3,5-tris-(4-nitrophenyl)benzene, on complete reaction with an excess of Sn/HCl\mathrm{Sn} / \mathrm{HCl}Sn/HCl gives a major product, which on treatment with an excess of NaNO2/HCl\mathrm{NaNO}_2 / \mathrm{HCl}NaNO2​/HCl at 0∘C0^{\circ} \mathrm{C}0∘C provides P\mathbf{P}P as the product. P\mathbf{P}P, upon treatment with excess of H2O\mathrm{H}_2 \mathrm{O}H2​O at room temperature, gives the product Q\mathbf{Q}Q. Bromination of Q\mathbf{Q}Q in aqueous medium furnishes the product R\mathbf{R}R. The compound P\mathbf{P}P upon treatment with an excess of phenol under basic conditions gives the product S\mathbf{S}S. The molar mass difference between compounds Q\mathbf{Q}Q and R\mathbf{R}R is 474 g mol−1474 \mathrm{~g} \mathrm{~mol}^{-1}474 g mol−1 and between compounds P\mathbf{P}P and S\mathbf{S}S is 172.5 g mol−1172.5 \mathrm{~g} \mathrm{~mol}^{-1}172.5 g mol−1.The total number of carbon atoms and heteroatoms present in one molecule of S\mathbf{S}S is ‾\underline{\hspace{2cm}}​. [Use : Molar mass (in gmol−1\mathrm{g} \mathrm{mol}^{-1}gmol−1): H=1,C=12, N=14,O=16,Br=80,Cl=35.5\mathrm{H}=1, \mathrm{C}=12, \mathrm{~N}=14, \mathrm{O}=16, \mathrm{Br}=80, \mathrm{Cl}=35.5H=1,C=12, N=14,O=16,Br=80,Cl=35.5 Atoms other than C\mathrm{C}C and H\mathrm{H}H are considered as heteroatoms]
Numerical answer
View written solutionFree

Correct answer: 51

  1. Starting compound and reduction

The given compound is 1,3,5-tris-(4-nitrophenyl)benzene.

It has three para-nitrophenyl groups attached to a central benzene ring.

On complete reduction with excess Sn/HCl\mathrm{Sn/HCl}Sn/HCl, each −NO2-\mathrm{NO_2}−NO2​ group is converted into −NH2-\mathrm{NH_2}−NH2​.

So the major product is:

1,3,5-tris-(4-aminophenyl)benzene1,3,5\text{-tris-(4-aminophenyl)benzene}1,3,5-tris-(4-aminophenyl)benzene
  1. Formation of P\mathbf{P}P

Treatment with excess NaNO2/HCl\mathrm{NaNO_2/HCl}NaNO2​/HCl at 0∘C0^\circ \mathrm{C}0∘C diazotizes each amino group:

−NH2→−N2+Cl−-\mathrm{NH_2} \to -\mathrm{N_2^+Cl^-}−NH2​→−N2+​Cl−

Hence P\mathbf{P}P is the tris-diazonium chloride derivative.

So P\mathbf{P}P contains 3 diazonium groups.


  1. Formation of Q\mathbf{Q}Q from P\mathbf{P}P

Diazonium salt on treatment with excess water at room temperature gives phenol:

−N2+Cl−→H2O−OH-\mathrm{N_2^+Cl^-} \xrightarrow{H_2O} -\mathrm{OH}−N2+​Cl−H2​O​−OH

Thus Q\mathbf{Q}Q is:

1,3,5-tris-(4-hydroxyphenyl)benzene1,3,5\text{-tris-(4-hydroxyphenyl)benzene}1,3,5-tris-(4-hydroxyphenyl)benzene

So Q\mathbf{Q}Q has 3 phenolic rings, each para-substituted.


  1. Formation of R\mathbf{R}R by bromination of Q\mathbf{Q}Q

A phenolic ring strongly activates bromination at the ortho positions to −OH-\mathrm{OH}−OH.

In each ppp-substituted phenol ring, the para position is already occupied by linkage to the central benzene ring, so bromination occurs at the two ortho positions.

Thus each outer ring gets 2 bromine atoms.

There are 3 such rings, so total bromines introduced:

3×2=63 \times 2 = 63×2=6

Mass increase from Q\mathbf{Q}Q to R\mathbf{R}R per bromination is replacement of H by Br:

80−1=7980 - 1 = 7980−1=79

For 6 brominations:

6×79=4746 \times 79 = 4746×79=474

This matches the given data, confirming the structure.


  1. Formation of S\mathbf{S}S from P\mathbf{P}P with phenol/basic medium

Diazonium salts couple with phenol in basic medium to give azo compounds.

Each diazonium group couples with one phenol molecule.

Since P\mathbf{P}P has 3 diazonium groups, S\mathbf{S}S is formed by coupling with 3 phenol molecules.

The mass difference between P\mathbf{P}P and S\mathbf{S}S is given as 172.5 g mol−1172.5\,\mathrm{g\,mol^{-1}}172.5gmol−1.

Let us verify per coupling.

For one coupling:

  • one phenol unit added: C6H6O\mathrm{C_6H_6O}C6​H6​O, mass =6(12)+6(1)+16=94= 6(12)+6(1)+16=94=6(12)+6(1)+16=94
  • one H is lost from phenol ring during coupling: −1-1−1
  • diazonium group loses N2\mathrm{N_2}N2​? No, in azo coupling the diazonium group becomes −N=N−-\mathrm{N=N}-−N=N−, so the two nitrogens remain in product.
  • chloride ion is not part of covalent structure of product.

So net increase per diazonium group from diazonium salt to azo-coupled product is:

94−1−35.5=57.594 - 1 - 35.5 = 57.594−1−35.5=57.5

For 3 groups:

3×57.5=172.53 \times 57.5 = 172.53×57.5=172.5

So indeed all 3 diazonium groups couple with phenol.

Hence S\mathbf{S}S is the tris-azo coupled product with 3 phenol units.


  1. Count carbon atoms in S\mathbf{S}S

Initial skeleton in starting trisubstituted benzene after diazotization still has:

  • central benzene ring: 666 carbons
  • three outer phenyl rings: 3×6=183 \times 6 = 183×6=18 carbons

So in P\mathbf{P}P (and retained in S\mathbf{S}S):

6+18=24 carbons6 + 18 = 24 \text{ carbons}6+18=24 carbons

Now 3 phenol molecules couple, each contributes one phenyl ring:

3×6=18 carbons3 \times 6 = 18 \text{ carbons}3×6=18 carbons

Total carbons in S\mathbf{S}S:

24+18=4224 + 18 = 4224+18=42
  1. Count heteroatoms in S\mathbf{S}S

Heteroatoms are atoms other than C and H.

In S\mathbf{S}S:

  • each azo linkage contributes 222 nitrogen atoms
  • there are 333 azo linkages

So nitrogen atoms:

3×2=63 \times 2 = 63×2=6

Each coupled phenol unit retains one oxygen atom:

3×1=33 \times 1 = 33×1=3

Total heteroatoms:

6+3=96 + 3 = 96+3=9
  1. Total number of carbon atoms and heteroatoms in S\mathbf{S}S
42+9=5142 + 9 = 5142+9=51

Therefore, the required integer is:

51\boxed{51}51​
  1. Comparison with stored correct answer

Stored correct answer = 515151.

Our derived answer also is 515151, so they agree.

PreviousNext

More from Compounds Containing Nitrogen

  • Considering the following reaction sequence, the correct option(s) is(are) Includes diagram2022 · Multiple correct
  • Match the compounds in LIST-I with the observations in LIST-II, and choose the correct option. Includes table2022 · MCQ
  • The reaction of Q with PhSNa yields an organic compound (major product) that gives positive Carius test on treatment with Na2​O2​ followed by addition of BaCl2​. The correct option(s) for Q is (are)2021 · Multiple correct
  • The reaction sequence(s) that would lead to o-xylene as the major product is(are)2021 · Multiple correct
  • Reaction of x g of Sn with HCl quantitatively produced a salt. Entire amount of the salt reacted with y g of nitrobenzene in the presence of required amount of HCl to produce 1.29 g of an organic salt (quantitatively). (Use Molar masses…2021 · Numerical
  • Correct option(s) for the following sequence of reactions is(are) Includes diagram2021 · Multiple correct
  • Reaction of x g of Sn with HCl quantitatively produced a salt. Entire amount of the salt reacted with y g of nitrobenzene in the presence of required amount of HCl to produce 1.29 g of an organic salt (quantitatively). (Use Molar masses…2021 · Numerical
  • Consider the reaction sequence from P to Q shown below. The overall yield of the major product Q from P is 75%. What is the amount in grams of Q obtained from 9.3 mL of P? (Use density of P = 1.00 g mL-1; Molar mass of C = 12.0, H = 1.0, O… Includes diagram2020 · Numerical