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Compounds Containing Nitrogen question

2009 · Shift 1 · Q20
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  5. /2009 · Shift 1 · Q20

Compounds Containing Nitrogen question

2009 · Shift 1 · Q20

JEE AdvancedChemistryCompounds Containing NitrogenMCQ+3 / −1

Match each of the compounds in Column I with its characteristic reaction(s) in Column II.

Column I Column II
(A) CH3CH2CH2CNC{H_3}C{H_2}C{H_2}CNCH3​CH2​CH2​CN (P) Reduction with Pd−C/H2Pd - C/{H_2}Pd−C/H2​
(B) CH3CH2OCOCH3C{H_3}C{H_2}OCOC{H_3}CH3​CH2​OCOCH3​ (Q) Reduction with SnCl2/HClSnC{l_2}/HClSnCl2​/HCl
(C) CH3−CH=CH−CH2OHC{H_3} - CH = CH - C{H_2}OHCH3​−CH=CH−CH2​OH (R) Development of foul smell on treatment with chloroform and alcoholic KOHKOHKOH
(D) CH3CH2CH2CH2NH2C{H_3}C{H_2}C{H_2}C{H_2}N{H_2}CH3​CH2​CH2​CH2​NH2​ (S) Reduction with diisobutylaluminium hydride (DIBAL-H)
(T) Alkaline hydrolysis

  1. A
    (A)→(P),(Q),(S),(T);(B)→(Q),(T);(C)→(P);(D)→(S)\mathrm{(A)\to(P),(Q),(S),(T);(B)\to(Q),(T);(C)\to(P);(D)\to(S)}(A)→(P),(Q),(S),(T);(B)→(Q),(T);(C)→(P);(D)→(S)
  2. B
    (A)→(Q),(R),(S),(T);(B)→(S),(T);(C)→(P);(D)→(R)\mathrm{(A)\to(Q), (R), (S),(T);(B)\to(S),(T);(C)\to(P);(D)\to(R)}(A)→(Q),(R),(S),(T);(B)→(S),(T);(C)→(P);(D)→(R)
  3. C
    (A)→(P),(R),(S),(T);(B)→(S),(T);(C)→(P);(D)→(R),(T)\mathrm{(A)\to(P),(R),(S),(T);(B)\to(S),(T);(C)\to(P);(D)\to(R), (T)}(A)→(P),(R),(S),(T);(B)→(S),(T);(C)→(P);(D)→(R),(T)
  4. D
    (A)→(P),(Q),(S),(T);(B)→(S),(T);(C)→(P);(D)→(R)\mathrm{(A)\to(P),(Q),(S),(T);(B)\to(S),(T);(C)\to(P);(D)\to(R)}(A)→(P),(Q),(S),(T);(B)→(S),(T);(C)→(P);(D)→(R)
View written solutionFree

Correct answer: D

This is a matching-type question where we need to pair compounds from Column I with their characteristic reactions from Column II.

Step-by-step Analysis:

1. Analysis of Compound (A): CH3CH2CH2CNCH_3CH_2CH_2CNCH3​CH2​CH2​CN (Butanenitrile) This is an alkyl cyanide (nitrile).

  • (P) Reduction with Pd−C/H2Pd-C/H_2Pd−C/H2​: Catalytic hydrogenation of nitriles reduces the cyano group (−CN-CN−CN) to a primary amino group (−CH2NH2-CH_2NH_2−CH2​NH2​). CH3CH2CH2CN+2H2→Pd−CCH3CH2CH2CH2NH2CH_3CH_2CH_2CN + 2H_2 \xrightarrow{Pd-C} CH_3CH_2CH_2CH_2NH_2CH3​CH2​CH2​CN+2H2​Pd−C​CH3​CH2​CH2​CH2​NH2​ So, (A) matches with (P).

  • (Q) Reduction with SnCl2/HClSnCl_2/HClSnCl2​/HCl: This is the Stephen reduction. Nitriles are first reduced to iminium salts, which upon hydrolysis yield aldehydes. CH3CH2CH2CN→HClSnCl2CH3CH2CH2CH=NH→H3O+CH3CH2CH2CHO+NH4+CH_3CH_2CH_2CN \xrightarrow[HCl]{SnCl_2} CH_3CH_2CH_2CH=NH \xrightarrow{H_3O^+} CH_3CH_2CH_2CHO + NH_4^+CH3​CH2​CH2​CNSnCl2​HCl​CH3​CH2​CH2​CH=NHH3​O+​CH3​CH2​CH2​CHO+NH4+​ So, (A) matches with (Q).

  • (S) Reduction with diisobutylaluminium hydride (DIBAL-H): DIBAL-H is a reducing agent that can partially reduce nitriles to imines, which on hydrolysis give aldehydes. CH3CH2CH2CN→1.DIBAL−H→2.H2OCH3CH2CH2CHOCH_3CH_2CH_2CN \xrightarrow{1. DIBAL-H} \xrightarrow{2. H_2O} CH_3CH_2CH_2CHOCH3​CH2​CH2​CN1.DIBAL−H​2.H2​O​CH3​CH2​CH2​CHO So, (A) matches with (S).

  • (T) Alkaline hydrolysis: Nitriles undergo hydrolysis in the presence of an acid or a base to form carboxylic acids or their salts. In alkaline medium, they form carboxylate salts. CH3CH2CH2CN+NaOH+H2O→CH3CH2CH2COONa+NH3CH_3CH_2CH_2CN + NaOH + H_2O \rightarrow CH_3CH_2CH_2COONa + NH_3CH3​CH2​CH2​CN+NaOH+H2​O→CH3​CH2​CH2​COONa+NH3​ So, (A) matches with (T).

Conclusion for (A): It matches with (P), (Q), (S), and (T).

2. Analysis of Compound (B): CH3CH2OCOCH3CH_3CH_2OCOC{H_3}CH3​CH2​OCOCH3​ (Ethyl acetate) This is an ester.

  • (S) Reduction with diisobutylaluminium hydride (DIBAL-H): At low temperatures (e.g., -78°C), DIBAL-H reduces esters to aldehydes. CH3COOCH2CH3→1.DIBAL−H,−78∘C→2.H2OCH3CHO+CH3CH2OHCH_3COOCH_2CH_3 \xrightarrow{1. DIBAL-H, -78^\circ C} \xrightarrow{2. H_2O} CH_3CHO + CH_3CH_2OHCH3​COOCH2​CH3​1.DIBAL−H,−78∘C​2.H2​O​CH3​CHO+CH3​CH2​OH So, (B) matches with (S).

  • (T) Alkaline hydrolysis: Esters undergo saponification (alkaline hydrolysis) to produce a carboxylate salt and an alcohol. CH3COOCH2CH3+NaOH→CH3COONa+CH3CH2OHCH_3COOCH_2CH_3 + NaOH \rightarrow CH_3COONa + CH_3CH_2OHCH3​COOCH2​CH3​+NaOH→CH3​COONa+CH3​CH2​OH This is a characteristic reaction of esters. So, (B) matches with (T).

  • Reactions (P), (Q), and (R) are not characteristic for esters.

Conclusion for (B): It matches with (S) and (T).

3. Analysis of Compound (C): CH3−CH=CH−CH2OHCH_3-CH=CH-CH_2OHCH3​−CH=CH−CH2​OH (But-2-en-1-ol) This is an unsaturated primary alcohol.

  • (P) Reduction with Pd−C/H2Pd-C/H_2Pd−C/H2​: Catalytic hydrogenation with H2/Pd−CH_2/Pd-CH2​/Pd−C is a standard method to reduce carbon-carbon double bonds. CH3−CH=CH−CH2OH+H2→Pd−CCH3−CH2−CH2−CH2OHCH_3-CH=CH-CH_2OH + H_2 \xrightarrow{Pd-C} CH_3-CH_2-CH_2-CH_2OHCH3​−CH=CH−CH2​OH+H2​Pd−C​CH3​−CH2​−CH2​−CH2​OH So, (C) matches with (P).

  • Reactions (Q), (R), (S), and (T) are not applicable to this compound. DIBAL-H does not reduce isolated double bonds or alcohols.

Conclusion for (C): It matches with (P).

4. Analysis of Compound (D): CH3CH2CH2CH2NH2CH_3CH_2CH_2C{H_2}NH_2CH3​CH2​CH2​CH2​NH2​ (Butan-1-amine) This is a primary aliphatic amine.

  • (R) Development of foul smell on treatment with chloroform and alcoholic KOHKOHKOH: This is the carbylamine (or isocyanide) test. It is a characteristic test for primary amines. The reaction produces a foul-smelling isocyanide. CH3CH2CH2CH2NH2+CHCl3+3KOH(alc.)→ΔCH3CH2CH2CH2NC+3KCl+3H2OCH_3CH_2CH_2CH_2NH_2 + CHCl_3 + 3KOH(alc.) \xrightarrow{\Delta} CH_3CH_2CH_2CH_2NC + 3KCl + 3H_2OCH3​CH2​CH2​CH2​NH2​+CHCl3​+3KOH(alc.)Δ​CH3​CH2​CH2​CH2​NC+3KCl+3H2​O So, (D) matches with (R).

  • Reactions (P), (Q), (S), and (T) are not applicable to a primary amine.

Conclusion for (D): It matches with (R).

Final Matching Summary:

  • (A) →\rightarrow→ (P), (Q), (S), (T)
  • (B) →\rightarrow→ (S), (T)
  • (C) →\rightarrow→ (P)
  • (D) →\rightarrow→ (R)

Comparing this with the options:

  • A: Mismatched (B) and (D).
  • B: Mismatched (A).
  • C: Mismatched (A) and (D).
  • D: Matches perfectly with our derived result.

Therefore, the correct option is D.

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