Section 9: Amines – Chapter 20

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Presentation transcript:

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 Basicity is often reported as the pKa of the conjugate acid:

Some representative pKa values: Amines: Basicity Some representative pKa values:

Amines: in Biology

Amines: in Biology

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

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.

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

Amines: Preparation E. Reductive amination Great reaction!!

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

Examples

Mechanism

Curtius rearrangement

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