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Compounds Containing Nitrogen question

2019 · 10 Apr · Shift 1 · Q20
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Compounds Containing Nitrogen question

2019 · 10 Apr · Shift 1 · Q20

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Ethylamine (C2H5NH2C_2H_5NH_2C2​H5​NH2​) can be obtained from N-ethylphatalimide on treatment with :
  1. A
    CaH2CaH_2CaH2​
  2. B
    H2OH_2OH2​O
  3. C
    NaBH4NaBH_4NaBH4​
  4. D
    NH2NH2NH_2NH_2NH2​NH2​
View written solutionFree

Correct answer: D

  1. Identify the reaction involved

    NNN-ethylphthalimide is a derivative of phthalimide. To obtain a primary amine from an NNN-alkylphthalimide, the standard method is the Gabriel phthalimide synthesis.

  2. Key principle of Gabriel synthesis

    In Gabriel synthesis:

    • Potassium phthalimide reacts with an alkyl halide to form NNN-alkylphthalimide.
    • Then, cleavage of the phthalimide group gives the primary amine.

    This cleavage is commonly done using hydrazine (NH2NH2)(NH_2NH_2)(NH2​NH2​).

  3. Apply to the given compound

    Here, the compound is NNN-ethylphthalimide. On treatment with hydrazine:

    N-ethylphthalimide→NH2NH2C2H5NH2+phthalhydrazideN\text{-ethylphthalimide} \xrightarrow{NH_2NH_2} C_2H_5NH_2 + \text{phthalhydrazide}N-ethylphthalimideNH2​NH2​​C2​H5​NH2​+phthalhydrazide

    Thus, ethylamine is liberated.

  4. Check the options

    • A: CaH2CaH_2CaH2​ — drying/reducing-type reagent, not used here.
    • B: H2OH_2OH2​O — simple water will not cleave NNN-ethylphthalimide to ethylamine.
    • C: NaBH4NaBH_4NaBH4​ — mild reducing agent; not used for Gabriel deprotection.
    • D: NH2NH2NH_2NH_2NH2​NH2​ — correct reagent for hydrazinolysis of NNN-alkylphthalimide.
  5. Conclusion

    The correct answer is:

    D  (NH2NH2)\boxed{D\; (NH_2NH_2)}D(NH2​NH2​)​

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