2009_14_Amines_II - Chem 2204/2206/2208 Wednesday Mar 11...

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Unformatted text preview: Chem 2204/2206/2208 Wednesday Mar 11 Lecture 13 Amines (I) Friday Mar 13 Lecture 14 Amines (II). TODAY 1 • Test 2 (Carboxylic Acids) . Test 2 solutions are posted on http://http-server.carleton.ca/~pbuist/ . Outline for Final exam now posted on course website! Overview of Lecture • Synthesis of Amines (5 routes) • Top Ten Reactions of Amines 2 Synthesis of amines : Amines are very important synthetic targets • Nobel Prize to William S. Knowles in 2001: Enantioselective Synthesis of L-DOPA 3 Dopamine- neurotransmitter L-DOPA (manages Parkinson’s disease) in vivo Synthesis of Primary Amines (R-NH 2 ) Route 1 : Alkylation of Ammonia Route 2: Azide /Reduction 4 Route 3: Gabriel Synthesis Route 4. Cyanide/ Reduction Route 5. Imine/Enamine formation/ Reduction 1. Synthesis of Primary Amines: Ammonia Alkylation Doesn’t work that well for synthesis of primary amines: R X R NH 2 5 R X NH 3 : R NH 3 X- + R NH 2 XH .. + R X This route is great for producing 4˚ salts Eg. 2. Synthesis of primary amines: Azide Reduction • This does work… no overalkylation R X R NH 2 6 X R N N + N-- Na + N N + N R LiAlH 4 R NH 2 N 2 + 3. Synthesis of primary amines: Gabriel Synthesis...
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2009_14_Amines_II - Chem 2204/2206/2208 Wednesday Mar 11...

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