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Compounds Containing Nitrogen question

2020 · 5 Sep · Shift 1 · Q6
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  5. /2020 · 5 Sep · Shift 1 · Q6

Compounds Containing Nitrogen question

2020 · 5 Sep · Shift 1 · Q6

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
The most appropriate reagent for conversion of C2H5CNC_2H_5CNC2​H5​CN into CH3CH2CH2NH2CH_3CH_2CH_2NH_2CH3​CH2​CH2​NH2​ is
  1. A
    NaBH4NaBH_4NaBH4​
  2. B
    CaH2CaH_2CaH2​
  3. C
    Na(CN)BH3Na(CN)BH_3Na(CN)BH3​
  4. D
    LiAlH4LiAlH_4LiAlH4​
View written solutionFree

Correct answer: D

  1. Identify the transformation

We need to convert:

C2H5CN  →  CH3CH2CH2NH2C_2H_5CN \;\to\; CH_3CH_2CH_2NH_2C2​H5​CN→CH3​CH2​CH2​NH2​

Here,

  • C2H5CN=CH3CH2C≡NC_2H_5CN = CH_3CH_2C\equiv NC2​H5​CN=CH3​CH2​C≡N (a nitrile, propanenitrile)
  • Product CH3CH2CH2NH2CH_3CH_2CH_2NH_2CH3​CH2​CH2​NH2​ is propylamine

So this is the reduction of a nitrile to a primary amine.

In general:

R−C≡N→hydrolysis/workupR−CH2NH2R-C\equiv N \xrightarrow[\text{hydrolysis/workup}]{} R-CH_2NH_2R−C≡Nhydrolysis/workup​R−CH2​NH2​

  1. Check the suitable reducing agent

A nitrile requires a strong reducing agent for conversion into a primary amine. The standard reagent is:

LiAlH4LiAlH_4LiAlH4​

Reaction:

R−C≡N→LiAlH4R−CH2NH2R-C\equiv N \xrightarrow{LiAlH_4} R-CH_2NH_2R−C≡NLiAlH4​​R−CH2​NH2​

Thus,

CH3CH2C≡N→LiAlH4CH3CH2CH2NH2CH_3CH_2C\equiv N \xrightarrow{LiAlH_4} CH_3CH_2CH_2NH_2CH3​CH2​C≡NLiAlH4​​CH3​CH2​CH2​NH2​

  1. Evaluate each option
  • A: NaBH4NaBH_4NaBH4​
    This is a mild reducing agent. It reduces aldehydes and ketones, but does not normally reduce nitriles.
    Hence, incorrect.

  • B: CaH2CaH_2CaH2​
    Calcium hydride is mainly used as a drying agent/base, not for reducing nitriles to amines.
    Hence, incorrect.

  • C: Na(CN)BH3Na(CN)BH_3Na(CN)BH3​
    Sodium cyanoborohydride is a mild reducing agent used mainly in reductive amination. It is not suitable for direct reduction of nitriles.
    Hence, incorrect.

  • D: LiAlH4LiAlH_4LiAlH4​
    Strong reducing agent; reduces nitriles to primary amines.
    Hence, correct.

  1. Conclusion

The most appropriate reagent is:

LiAlH4\boxed{LiAlH_4}LiAlH4​​

So the correct option is D.

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