Introduction to Organic Chemistry
Prof. Mike Southern(12 lectures)
This course gives a basic introduction to organic synthesis. The aim is to show the use of several common reactions, introduce the concept of synthetic organic chemistry and how organic chemists design and carry out multi step synthesis. Several new organic reactions are introduced on the way but most mechanistic aspects are dealt with later.
Recommended reading:
This course contains material that can be found in most textbooks on organic synthetic chemistry. I recommend the following books for guidance:
General reading material:
Clayden, Greeves, Warren and Wothers: Organic Chemistry, Oxford University Press, 2001.
Graham Solomon and Craig Fryhle: Organic Chemistry 7th edition.
Specific reading material:
Mackie, Smith and Aitken: Guidebook to Organic Synthesis 3rd. ed. Longman, 1999.
Warren: Organic Synthesis: The Disconnection Approach, John Wiley and Sons, 1993.
Warren: Designing Organic Synthesis: A Programmed Introduction to the Synthon Approach, John Wiley and sons, 1996.
The following topics will be covered in this course:
Introduction to synthesis, chemoselectivity, regioselectivity, functional groups, revision of common functional groups: halides, alcohols, amines, alkenes, aromatic compounds, reduction, oxidation, Functional Group Interconversion (FGI), synthons, synthetic equivalent, target molecule, making simple carbon-carbon bonds, radical, carbocation, carbanion, retrosynthesis, retrosynthetic analysis, electrophilic carbon, nucleophilic carbon, Grignard reagents, organocopper compounds, alkyl lithium compounds, stabilised carbanions, order of stability, triphenylphosphonium ylide, carbanion stabilised by two electron withdrawing groups, acid/base activation, pKa of organic reagents, nucleophilicity vs. basicity, malonate ester, enolate formation, alkylation of malonate esters, double alkylation reactions, C-alkylation vs. O-alkylation, decarboxylation, kinetic vs. thermodynamic control, β-keto esters, 1,3-diketone, condensation reactions (Knoevenagel, Aldol etc.), imine, Michael addition, reductive amination, pericyclic reactions, Diels-Alder reaction, diene, and dienophiles, 1,3- dipolar cycloaddition, cisoid/transoid, protecting groups: amine, carbamates, benzyloxycarbonyl, t-butoxycarbonyl, carboxylic esters.
Stereochemistry:
These lectures deal with the conformations of organic molecules, and their three-dimensional orientation in space. It is an advantage to have 'ball-and-stick' molecular modelling aids for visualisation but several visualisation packages are also available on-line.
Recommended reading lists will be provided at later date, but the main text book used will be: 'Stereochemistry' by David G. Morris, Tutorial Chemistry Text, Royal Society of Chemistry, 2001, ISBN 0-85404-602-X.
The following topics will be covered in this course:
Isomers (contributional isomers, conformers, stereoisomers), Newman projection, anti/gauche, achiral molecules, chiral molecules, stereogenic centres, enantiomers, diastereoisomers, test for chirality, nomenclature of enantiomers, Cahn-Ingold-Prelog convention, optical activity, amino acids, peptides (helixes, sheets), racemisation (racemates), effects on drugs, separation of enantiomers (resolution), chromatography, Fisher projection, enantiomeric excess, enantiomeric ratio, molecules with two (or more) stereogenic centres, diastereotopic compounds (diastereomers) epimers, meso compounds, erythro/threo, syn/anti, diastereomeric excess, Fisher projection of compounds with more than one stereogenic centre, chirality without stereogenic centres: allenes, biphenyls, amines, ammonium salts, oximes, sulfur, stereoisomers in cyclic structures, cylopropane, cyclobutane, cyclohexane, Pitzer and Baeyer strain, carbohydrates, anomeric effect, steroids, prochirality, enantiotopic groups, enantiotopic faces, chemical reactions, substitution reactions, unsaturated carbons, asymmetric synthesis, special topics