Organic Synthesis I

The subject covers principals, reaction types, reagents and mechanism for preparation of organic molecules with applications in medicinal and material sciences. Processes with specific safety, waste and environmental issues are highlighted. Details: Reagent selection, reaction mechanisms, pKa and choice of base, solvent effects, alkylation of carbonyl compounds, nitriles, nitro-compounds, imines and enamines, metal enolates, enol ethers, kinetic and thermodynamic control, modern Aldol type reactions, condensation reactions with carbonyl compounds, alkenes from carbonyl compounds, phosphorus ylides, phosphonate anions, sulphur ylides and their reactivity, conjugated addition. Transformation of functional groups by substitution reactions, protecting groups, electrophilic addition to C-C double and triple bonds, hydroboration, reactions with organoboranes, reduction of carbonyl, C-C double and triple bonds, hydrogenation, hydride reductions. Pericyclic reactions: cycloadditions, sigmaotroptic rearrangements, electrocyclic reactions, group transfer reactions, frontier molecular orbital theory. Introduction to retro synthesis

Upon completion of the coarse the student should within the framework of the coarse content: - Be able to plan the synthesis of organic molecules with respect to reagents and reaction conditions. - Should know and be able to explain reaction mechanisms. - Should be able to identify major by-products in reactions. - Be able to use frontier molecular orbital theory to predict the outcome of pericyclic reactions. - Be able to name important reactions. - Should understand how functional groups affect electron density, properties and reactivity in organic compounds. - Should be able to estimate the pKa values for carboxylic acids, amines, alcohols and ketones in the presence of various functionalities. - Be able to explain how the choice of base affects reactivity, hazard of operation and the price of processes. -Be able to identify processes/reactions that give a lot of waste. -Know which metals are environmentally problematic.

Lectures and exercises.

Expected work load in the course is 200-225 hours.

To take the exam, participation in 7 out of 9 exercises is required.