This module aims to build on the strong foundation in the fundamental principles of chemical reactivity, and physical-organic chemistry concepts. It extends the students' knowledge of key organic functional groups and how they react to form a variety of products using reaction pathways commonly used to make drugs and related compounds. Particular emphasis is placed on reactions involving carbonyl group-containing compounds. The use of IR and NMR spectroscopy in monitoring organic reactions and characterising organic compounds will be expanded on. The module also introduces the student to the conformational and 3-dimensional properties of organic compounds, how they can be analysed and used to infer reaction mechanisms.
Carbonyl Group Chemistry and Condensation Reactions
Draw and discuss the mechanisms of the aldol, Claisen, Dieckmann, Knoevenagel, Grignard and Wittig reactions; Use of protecting groups in carbonyl chemistry; Use of compounds containing carbonyl groups for the synthesis of simple heterocycles – reactions of aldehydes and ketones with amines to form imines (imine-enamine tautomerism, Schiff bases); Use of Organolithium reagents in enolate chemistry; Use of IR and NMR spectroscopy for monitoring carbonyl functional group changes and characterising products. Target synthesis of molecules containing carbonyl groups – target molecule route identification (identification of simple disconnections, functional group interconversions, synthons and synthetic equivalents).
Stereochemical Aspects in Organic Chemistry
Identification of stereogenic centres, enantiomers, diastereoisomers, and meso compounds – correct use of Cahn-Ingold-Prelog rules to identify each stereogenic centre’s configuration (e.g. R and S) – drawing Fischer and Haworth projects; Regioselective, stereoselective and stereospecific reactions including the Diels-Alder reaction – drawing and explaining mechanisms; Syn- and anti-addition to alkenes and cyclic alkenes – carbocation (and rearrangements)and bromonium ion intermediates; Important asymmetric reactions including Sharpless asymmetric epoxidation and dihydroxylation reactions; Control of the stereochemical outcome of a reaction – substrate control, reagent control and catalyst control.
|Module Content & Assessment