19_lec_19_20_06 - sp 3 N by C-N connectivity primary amine...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
Unit V. Amines Unit V. Amines A. Introduction 1. Structure 2. Nomenclature 3. Chirality 4. Basicity B. Synthesis of Amines 1. Alkylation a. S N 2 b. Gabriel Synthesis 2. Reductive Amination 3. Acylation-Reduction 4. Reduction of Azides 5. Reduction of Nitriles 6. Hofmann Rearrangement C. Reactions of Amines 1. Eliminations a. Hofmann b. Cope 2. Formation of Diazonium Salts a. Alkyl Amines b. Aryl Amines c. Example Suggesting reading : Chapter 24 Suggested problems: 24.30, 24.31, 24.35-24.46, 24.49, 24.50, 24.53, 24.54, 24.56, 24.61-24.63 AMINES! (smell bad - fishy) AMINES! (smell bad - fishy) NH 2 Methamphetamine N N H 2 N Putresine HO O Ph Lidocaine H N Me H 2 N Cadavarine CH 3 NH 2 HO O H N CH 3 Me H 3 C N O Morphine (Crystal Meth) CH 3 N O N CH 3 CH 3 O O HO NH 2 N HN H O Serotonin Lysergic acid diethylamide Cocaine (LSD) 1
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
2. Nomenclature 2. Nomenclature c. Classification of
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

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...
View Full Document

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.

Page1 / 2

19_lec_19_20_06 - sp 3 N by C-N connectivity primary amine...

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online