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Reductive Amination quiz

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  • What functional group is formed when a ketone or aldehyde reacts with a primary amine in an acidic environment?
    An imine is formed when a ketone or aldehyde reacts with a primary amine in an acidic environment.
  • What is the key intermediate called in the imine formation mechanism?
    The key intermediate is called the iminium cation, where the nitrogen has a positive charge.
  • What reducing agent is commonly used in reductive amination?
    Sodium cyanoborohydride (NaBH3CN) is commonly used as the reducing agent in reductive amination.
  • Why is NaBH3CN considered a mildly reducing agent?
    NaBH3CN is mildly reducing because the cyanide group is electron-withdrawing, making the reducing agent less reactive.
  • What is the final product of reductive amination when starting with a ketone or aldehyde and a primary amine?
    The final product is a primary amine.
  • What happens to the double bond in the imine during reductive amination?
    The double bond is reduced to a single bond, converting the imine into an amine.
  • What is the role of the reducing agent in reductive amination?
    The reducing agent adds hydrogen to the imine, reducing it to an amine.
  • Why is it important that NaBH3CN is only mildly reducing in this reaction?
    Its mild nature prevents unwanted byproducts and selectively reduces the imine without affecting other functional groups.
  • What is the difference between an imine and an enamine?
    An imine has a double bond between carbon and nitrogen, while an enamine has the double bond between carbon atoms adjacent to the nitrogen.
  • What is the first step in the reductive amination mechanism?
    The first step is the formation of an imine from a carbonyl compound and a primary amine in acid.
  • What happens if you deprotonate the iminium cation instead of reducing it?
    Deprotonation of the iminium cation yields an imine.
  • How does the hydrogen from NaBH3CN interact with the iminium cation?
    The hydrogen attacks the carbon of the iminium cation, pushing electrons up to the nitrogen and forming an amine.
  • What is the charge on the nitrogen in the iminium cation intermediate?
    The nitrogen in the iminium cation has a positive charge.
  • Why is sodium present in NaBH3CN, and what happens to it during the reaction?
    Sodium acts as a counterion to balance the negative charge on boron and is released into solution during the reaction.
  • What is the main advantage of using reductive amination in organic synthesis?
    Reductive amination is a convenient way to synthesize amines from carbonyl compounds and amines in one sequence.