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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o1165

Which of the following statements about enamines and imines are correct?

  1. AA tertiary amine and a ketone give an enamine on heating with acid.
  2. BEnamines react with electrophiles at the carbon beta to nitrogen.
  3. CAqueous acid hydrolyses an enamine back to the ketone and the amine.
  4. DA ketone and a primary amine normally give an imine rather than an enamine.

Answer: B, C, D

The N lone pair is conjugated with C=C, which makes the beta carbon nucleophilic. Enamine formation is reversible, and aqueous acid regenerates the carbonyl compound. Primary amines give imines because the carbinolamine loses water to form C=N. A tertiary amine has no N-H and cannot form an enamine through an iminium ion.
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