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Section 9: Amines – Chapter 20

Section 9: Amines – Chapter 20. Practice Problems:. None! ( yay !). Amines: Nomenclature. Amines: Heterocyclic Amines. Amines: Structure. note: if R, R’, R’’ are different , the amine is technically chiral , but… . Amines: Smell. Amines: Basicity.

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Section 9: Amines – Chapter 20

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  1. Section 9: Amines – Chapter 20 Practice Problems: None! (yay!)

  2. Amines: Nomenclature

  3. Amines: Heterocyclic Amines

  4. Amines: Structure note: if R, R’, R’’ are different, the amine is technically chiral, but…

  5. Amines: Smell

  6. Amines:Basicity Basicity is often reported as the pKa of the conjugate acid:

  7. Amines:Basicity Some representative pKa values:

  8. Amines: in Biology

  9. Amines: in Biology

  10. Amines: Preparation A. Reduction of nitriles / amides / nitro compounds

  11. Amines: Preparation B. SN2 reactions  If you want to go from a 2o amine to a 3o amine, rxn with R-X is usually OK. Otherwise, consider an alternative approach.

  12. Amines: Preparation C. Attack with NaN3 D. Gabriel Synthesis

  13. Amines: Preparation E. Reductive amination Great reaction!!

  14. 4D. Preparation of Primary Amines through the Hofmann and Curtius Rearrangements • Hofmann rearrangement

  15. Examples

  16. Mechanism

  17. Curtius rearrangement

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