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10.9: Nucleophilic Carbonyl Addition Reactions (Summary)

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    Before moving on to the next chapter, you should be confident in your ability to:

    • Recognize aldehyde and ketone groups in organic biomolecules
    • Draw/explain the bonding picture for aldehyde and ketone groups
    • Explain why the carbonyl carbon in an aldehyde or ketone is electrophilic
    • Draw complete curved arrow mechanisms for the following reaction types:
      • formation of a hemiacetal/hemiketal
      • collapse of a hemiacetal/hemiketal to revert to an aldehyde/ketone
      • formation and hydrolysis of an acetal/ketal
      • formation and hydrolysis of an N-glycosidic bond
      • formation and hydrolysis of an imine
      • transimination
    • Explain how the carbocation intermediates in glycosidic bond formation and hydrolysis reactions are stabilized by resonance
    • Explain the stereochemical considerations of a nucleophilic addition to an aldehyde/ketone, especially in the context of glycosidic bond formation. Be able to identify the re and si faces of an aldehyde, ketone, or imine.
    • In addition to these fundamental skills, you should develop your confidence in working with end-of-chapter problems involving more challenging, multi-step biochemical reactions.

    This page titled 10.9: Nucleophilic Carbonyl Addition Reactions (Summary) is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by Tim Soderberg via source content that was edited to the style and standards of the LibreTexts platform; a detailed edit history is available upon request.