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Understanding Aldehydes, Ketones, and Their Reactions in Organic Chemistry

This text delves into the chemistry of aldehydes and ketones, highlighting key reactions and mechanisms such as alpha substitution and carbonyl condensations. It addresses the condensation process, with a focus on aldol and Claisen reactions, distinguishing between symmetrical and mixed aldol products. The text also explores stability considerations in product formation, the significance of acidic protons, and intramolecular reactions. Key applications, including enamine synthesis and its role in gluconeogenesis, are discussed, emphasizing the importance of these reactions in organic synthesis.

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Understanding Aldehydes, Ketones, and Their Reactions in Organic Chemistry

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Presentation Transcript

  1. Examples: Aldehydes and ketones

  2. Add quickly Conditions for Alpha Substitution

  3. Conditions for Carbonyl Condensations

  4. “Condensation” drives the overall reaction (notice equilibrium arrows)

  5. Synthesis: Two products can be formed by the aldol

  6. Symmetrical vs. Mixed Aldol

  7. Example: Single product mixed Aldol No acidic protons

  8. Example: Single product mixed Aldol These protons are more acidic, thus easier to remove

  9. Watch out for the possibility of mixture of products In this case no mixture… why? – stability of pdt

  10. Example: Mixed Claisen No acidic hydrogens

  11. Example: Mixed Claisen-“like” A mixed aldol – Claisen type reaction

  12. Example: Intramolecular Claisen

  13. Intramolecular Claisen: Application to Synthesis • The β-keto ester formed still has one acid hydrogen and thus can do additional chemistry. • Remember, the β-keto ester formed can be hydrolyzed to the β-keto acid and these can spontaneously decarboxylate.

  14. Review: Synthesis of an enamine

  15. Enamine’s react similar to enolates

  16. Example: Stork Reaction

  17. Example: Robinson Annulation

  18. Biological Claisen

  19. Glucose Biosynthesis (Gluconeogenesis)

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