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NEET CHEMISTRYMedium

D is N-methyl aniline in the given below sequence of reaction: AreductionBCHCl3/KOHCreductionDA \xrightarrow{\text{reduction}} B \xrightarrow{CHCl_3/KOH} C \xrightarrow{\text{reduction}} D. Structure of A can be:

A

Option 1 (Missing)

B

Nitrobenzene

C

CH3NH2

D

Option 4 (Missing)

Step-by-Step Solution

Let's deduce the reaction sequence in reverse:

  1. Compound D: Given as N-methyl aniline (C6H5NHCH3C_6H_5-NH-CH_3), which is a secondary amine.
  2. Compound C: Formed by the reaction of B with CHCl3CHCl_3 and KOH, and upon reduction gives D. The reaction of a primary amine with CHCl3/KOHCHCl_3/KOH is the Carbylamine reaction, which yields an isocyanide (RNCR-NC). Reduction of an isocyanide (RNC+4[H]RNHCH3R-NC + 4[H] \rightarrow R-NH-CH_3) always produces a secondary amine with one methyl group. Since D is N-methyl aniline, C must be phenyl isocyanide (C6H5NCC_6H_5-NC).
  3. Compound B: Since B undergoes the carbylamine reaction to form phenyl isocyanide, B must be the corresponding primary aromatic amine, aniline (C6H5NH2C_6H_5-NH_2).
  4. Compound A: A is reduced to form aniline (B). The most common precursor that yields aniline upon reduction is nitrobenzene (C6H5NO2C_6H_5-NO_2).

Therefore, the structure of A is nitrobenzene.

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