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Compounds Containing Nitrogen question

2019 · 10 Apr · Shift 2 · Q21
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Compounds Containing Nitrogen question

2019 · 10 Apr · Shift 2 · Q21

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Which of the following is not a correct method of the preparation of benzylamine from cyanobenzene ?
  1. A
    (i) SnCl2SnCl_2SnCl2​ + HClHClHCl(gas) (ii) NaBH4NaBH_4NaBH4​
  2. B
    H2H_2H2​/NiNiNi
  3. C
    (i) LiAlH4LiAlH_4LiAlH4​ (ii) H3O+H_3O^+H3​O+
  4. D
    (i) HClHClHCl/H2OH_2OH2​O (ii) NaBH4NaBH_4NaBH4​
View written solutionFree

Correct answer: A, D

  1. Identify the starting compound and target product

Cyanobenzene is benzonitrile, with structure: C6H5−C≡NC_6H_5-C\equiv NC6​H5​−C≡N

The target product is benzylamine: C6H5−CH2NH2C_6H_5-CH_2NH_2C6​H5​−CH2​NH2​

So we need to convert a nitrile into a primary amine.

A nitrile on reduction gives: R−C≡N→reductionR−CH2NH2R-C\equiv N \xrightarrow[\text{reduction}]{} R-CH_2NH_2R−C≡Nreduction​R−CH2​NH2​


  1. Check each option

Option B: H2/NiH_2/NiH2​/Ni

Catalytic hydrogenation of nitriles reduces them to primary amines: C6H5−C≡N+2H2→NiC6H5−CH2NH2C_6H_5-C\equiv N + 2H_2 \xrightarrow{Ni} C_6H_5-CH_2NH_2C6​H5​−C≡N+2H2​Ni​C6​H5​−CH2​NH2​ So B is a correct method.


Option C: (i) LiAlH4LiAlH_4LiAlH4​ (ii) H3O+H_3O^+H3​O+

LiAlH4LiAlH_4LiAlH4​ is a standard reagent for reducing nitriles to primary amines: C6H5−C≡N→2. H3O+1. LiAlH4C6H5−CH2NH2C_6H_5-C\equiv N \xrightarrow[2.\ H_3O^+]{1.\ LiAlH_4} C_6H_5-CH_2NH_2C6​H5​−C≡N1. LiAlH4​2. H3​O+​C6​H5​−CH2​NH2​ So C is a correct method.


Option A: (i) SnCl2+HClSnCl_2 + HClSnCl2​+HCl(gas) (ii) NaBH4NaBH_4NaBH4​

This is Stephen reduction. A nitrile is first reduced to an iminium salt, which on hydrolysis gives an aldehyde: C6H5−C≡N→SnCl2/HCliminium salt→H2OC6H5−CHOC_6H_5-C\equiv N \xrightarrow{SnCl_2/HCl} \text{iminium salt} \xrightarrow{H_2O} C_6H_5-CHOC6​H5​−C≡NSnCl2​/HCl​iminium saltH2​O​C6​H5​−CHO Then NaBH4NaBH_4NaBH4​ reduces benzaldehyde to benzyl alcohol, not benzylamine: C6H5−CHO→NaBH4C6H5−CH2OHC_6H_5-CHO \xrightarrow{NaBH_4} C_6H_5-CH_2OHC6​H5​−CHONaBH4​​C6​H5​−CH2​OH Therefore this sequence does not give benzylamine.

So A is not a correct method.


Option D: (i) HCl/H2OHCl/H_2OHCl/H2​O (ii) NaBH4NaBH_4NaBH4​

Acidic hydrolysis of benzonitrile gives benzoic acid: C6H5−C≡N→HCl/H2OC6H5−COOHC_6H_5-C\equiv N \xrightarrow{HCl/H_2O} C_6H_5-COOHC6​H5​−C≡NHCl/H2​O​C6​H5​−COOH Now NaBH4NaBH_4NaBH4​ is a mild reducing agent. It reduces aldehydes and ketones, but does not reduce carboxylic acids under ordinary conditions. So benzoic acid will not be converted to benzylamine.

Hence D is also not a correct method.


  1. Conclusion

Among the given options, A and D both are not correct methods for preparing benzylamine from cyanobenzene.

Since the question is marked as MCQ (single correct) but two options are incorrect, the stored answer appears incomplete/incorrect.

Therefore, the chemically correct conclusion is: A and D\boxed{A \text{ and } D}A and D​

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