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NEET CHEMISTRYAminesMedium

Question

An organic compound (C3H9NC_3H_9N) (A), when treated with nitrous acid, gave an alcohol, and N2N_2 gas was evolved. (A) on warming with CHCl3CHCl_3 and caustic potash gave (C) which on reduction gave isopropylmethylamine. The structure of (A) is:

A

CH3CH2CH2NH2CH_3CH_2CH_2-NH_2

B

CH3CH2NHCH3CH_3CH_2-NH-CH_3

C

(CH3)3N(CH_3)_3N

D

(CH3)2CHNH2(CH_3)_2CH-NH_2

Step-by-Step Solution

Let us deduce the structure of compound A step-by-step:

  1. Reaction with Nitrous Acid (HNO2HNO_2): Compound A (C3H9NC_3H_9N) reacts with HNO2HNO_2 to yield an alcohol and N2N_2 gas. This is a characteristic reaction of primary aliphatic amines. Secondary and tertiary amines do not release nitrogen gas with HNO2HNO_2.
  2. Carbylamine Reaction: Compound A warms with CHCl3CHCl_3 and caustic potash (KOH) to give compound C. This is the Carbylamine test, which is exclusively given by primary amines to form foul-smelling isocyanides (carbylamines). Thus, C is an alkyl isocyanide (RNCR-NC).
  3. Reduction of C: Isocyanide C (RNCR-NC) on reduction gives isopropylmethylamine, which is a secondary amine with the structure (CH3)2CHNHCH3(CH_3)_2CH-NH-CH_3. Reduction of an isocyanide always yields a secondary amine with one methyl group: RNC+4[H]RNHCH3R-NC + 4[H] \rightarrow R-NH-CH_3. Comparing RNHCH3R-NH-CH_3 with the product (CH3)2CHNHCH3(CH_3)_2CH-NH-CH_3, we can identify the alkyl group 'RR' as the isopropyl group (CH3)2CH(CH_3)_2CH-.
  4. Conclusion: Since the alkyl group is isopropyl, the original primary amine 'A' must be isopropylamine, (CH3)2CHNH2(CH_3)_2CH-NH_2.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Amines. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAminesorganiccompoundtreatednitrousalcohol

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