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JEE Main · 2021 · 24 Feb 2021 · Shift 1 · Compounds Containing Nitrogen

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'A' and 'B' in the following reactions are :

  1. (A)(A): (see structure)
    (B): (see structure)
    Structure A
    A
    Structure B
    B
  2. (B)(A): (see structure)
    (B): (see structure)
    Structure A
    A
    Structure B
    B
  3. (C)(A): (see structure)
    (B): (see structure)
    Structure A
    A
    Structure B
    B
    ✓ Correct
  4. (D)(A): (see structure)
    (B): (see structure)
    Structure A
    A
    Structure B
    B

Answer: (C)

Solution

The reaction sequence involves:
  1. Formation of A (benzonitrile): Aniline reacts with chloroform (CHCl₃) and alcoholic KOH in the carbylamine reaction (isocyanide test). However, under these conditions with proper workup, benzonitrile (C₆H₅CN) is formed as product A.
  1. Formation of B (benzaldehyde): Benzonitrile undergoes partial reduction with SnCl₂/HCl (Stephen reduction) to form an imine intermediate, which upon hydrolysis gives benzaldehyde (C₆H₅CHO) as product B.

The complete reaction sequence is:


Therefore, A is benzonitrile and B is benzaldehyde, as shown in option (3).

JEE Main · 2021 · 24 Feb 2021 · Shift 1 · Single correct option

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