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Fundamentals of Organic ChemistryChemistryAmines

Which of the following methods can be used for eliminating the nitrogen atom of an amine present outside a ring?

Options

  1. AEmde degradation
  2. BHofmann elimination
  3. CBoth Hofmann and Cope eliminations
  4. DCope elimination

Correct answer

C. Both Hofmann and Cope eliminations

Step-by-step solution

Hofmann elimination involves the exhaustive methylation of an amine to form a quaternary ammonium salt, followed by heating with moist silver oxide ( Ag ₂ O / H ₂ O ) to yield an alkene and a tertiary amine. This effectively eliminates the nitrogen atom from the carbon chain. Cope elimination involves the oxidation of a tertiary amine to an amine oxide, which upon heating undergoes a syn-elimination to form an alkene and a hydroxylamine, also eliminating the nitrogen atom from the carbon chain. Both methods are sta

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