8.S: 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.

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