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JEE MainChemistryAldehydes and Ketones

An unknown straight-chain primary amine 'A' is treated with NaNO ₂/ HCl to yield compound 'B'. Compound 'B' on treatment with PCC gives compound 'C'. When 'C' is heated with dilute NaOH , the major product formed is 2-ethylhex-2-enal. The IUPAC name of the starting amine 'A' is:

Options

  1. APropan-1-amine
  2. BButan-1-amine
  3. CButan-2-amine
  4. DPentan-1-amine

Correct answer

B. Butan-1-amine

Step-by-step solution

Retrosynthetic analysis of 2-ethylhex-2-enal reveals it is the self-aldol condensation product of butanal. 2 CH ₃ CH ₂ CH ₂ CHO dil. NaOH, CH ₃ CH ₂ CH ₂ CH = C ( CH ₂ CH ₃) CHO (2-ethylhex-2-enal) Therefore, compound 'C' must be butanal. For 'C' to be an aldehyde, the precursor 'B' must be a primary alcohol, specifically butan-1-ol, since PCC oxidizes primary alcohols to aldehydes. Consequently, the starting amine 'A' that yields butan-1-ol upon reaction with nitrous acid ( NaNO ₂/ HCl ) is butan-1-amine. Answer:

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