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Introduction to Photostability
A Practical Introduction to
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Mastering the Art of Writing Reasonable Organic Reaction Mechanisms
| Type | Course |
|---|---|
| Language | English |
| Date |
August 17, 2009
to August 18, 2009 |
| Venue |
Four Points By Sheraton 1201 K Street NW Washington, DC 20005 US |
| Chemistry Specialties |
|
| Chemistry Techniques |
|
| Contact |
American Chemical Society 1155 Sixteenth Street, NW Washington, DC 20036 US (800) 227-5558 shortcourses@acs.org |
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This course is aimed at B.S. and M.S. chemists in the pharmaceutical and contract syntheses industries looking to improve upon their ability to draw a reasonable mechanism for any complex organic transformation. Registrants will need to purchase a copy of The Art of Writing Reasonable Organic Reaction Mechanisms, 2nd edition, in addition to their registration before the course starts. You should read sections 1.1 to 1.3 and work the corresponding problems at the end of Chapter 1 before arriving to the course. Bring the text to the course.
Key Topics
* How to identify what major class of mechanism is operative.
* How to get started at drawing a mechanism.
* When to draw proton-transfer steps under basic and acidic conditions.
* The fundamental reactions of carbocations.
* The fundamental organometallic reactions.
* The fundamental pericyclic reactions.
* The major mechanisms for substitution at C(sp3) and C(sp2) under various conditions.
* The mechanisms of typical pericyclic heterocycle-forming reactions.
Session titles
Agenda
* Basic Concepts - Conventions and first steps; polar mechanisms: nucleophiles, electrophiles, leaving groups; acids, bases, the pKa rule; free-radical mechanisms: chain and nonchain; pericyclic and transition-metal-mediated and -catalyzed mechanisms.
* Polar Mechanisms under Basic Conditions - Substitution and elimination at C(sp3) via SN2, E2, and E1cb; addition to C(sp2); substitution at C(sp2); substitution at C(sp3) via other mechanisms; migratory mechanisms; multistep mechanisms.
* Polar Mechanisms under Acidic Conditions - Formation and typical reactions of carbocations; substitution and elimination at C(sp3) via SN1, E1, and SN2; electrophilic addition to alkenes; electrophilic aromatic substitution; aromatic substitution via diazonium ions; nucleophilic addition to and substitution at electrophilic π bonds.
* Pericyclic Mechanisms - Identifying and naming the four major types; dipolar cycloadditions; Fischer indole synthesis; Claisen and Cope rearrangements; sigmatropic rearrangements that aren't.
* Transition-Metal-Mediated and Catalyzed Mechanisms - Conventions; fundamental mechanistic steps; addition reactions, including hydrogenation, hydroformylation, epoxidation, and dihydroxylation; substitution reactions catalyzed by Pd and other metals, including hydrogenolysis, Heck reaction, cross-couplings, Trost–Tsuji reaction; rearrangements and eliminations, including alkene metathesis and alcohol oxidation.