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Unformatted text preview: sp 3 N by C-N connectivity primary amine 1 o secondary amine 2 o tertiary amine 3 o R N H H R N R H R N R R R N R R R ammonium ion 4 o N H N H O N H N H NH 2 piperidine morpholine pyrrolidine aziridine aniline b. Common Names Amine Summary Amine Summary From: 1. Alkyl halide S N 2 (overalkylation) Gabriel Synthesis (1 o ) Azide reduction (adds -NH 2 ) Nitrile reduction (adds -CH 2 NH 2 ) 2. Aldehyde/ketone - Reductive amination H 2 NOH for 1 o , RNH 2 for 2 o , R 2 NH for 3 o 3. Acyl Chloride - Acylation-Reduction (adds -R) NH 3 for 1 o , RNH 2 for 2 o , R 2 NH for 3 o 4. Amide - Hofmann Rearrangement 5. Ar-NO 2 (H 2 /Pd) To: 1. Alkene Hofmann Elimination Cope Elimination 2. Diazonium Salt (NaNO 2 , HCl) Ar-Br (CuBr) Ar-Cl (CuCl) Ar-CN (CuCN) Ar-OH (H 3 O + /H 2 O) Ar-H (H 3 PO 2 ) Ar-I (KI) 2...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.
- Spring '03