This module is at an intermediate level and builds on carbonyl chemistry and stereochemistry content of the year 2 modules. The reactions of carbonyl compounds are some of the most important in organic chemistry and will be described in detail. The mechanistic aspects of these reactions will be emphasised. The varying biological activity of stereoisomers means that it is often necessary to prepare stereochemically pure compounds and an understanding of this chemistry is therefore a very important aspect of pharmaceutical chemistry. This module will examine this area in more detail and will consider the stereochemical outcomes of common organic reactions.
The practical element of the module continues to introduce new techniques required for the synthesis and characterisation of organic compounds, building on skills acquired during the semester 1 module, while supporting and reinforcing the concepts discussed in the lectures.
Conformational analysis of substituted cyclohexanes and related compounds, optical purity, % enantiomeric excess, molecules with more than one stereocentre (diastereomers), meso compounds, centres of symmetry, chirality without a chiral carbon (e.g. allenes, biphenyls). Introduction to dynamic stereochemistry: relative and absolute configuration, enantiotopic and diastereotopic hydrogens, prochirality, stereochemical consequences of nucleophilic substitution, electrophilic addition to alkenes, nucleophilic addition to aldehydes and ketones and elimination reactions.
Formation of imines and enamines, acetal formation, the Wittig reaction. Carbonyl chemistry at the alpha-position: Keto-enol tautomerism, enolates, reactions that involve deprotonation of the a-proton including the aldol reaction and condensation. alpha,beta-Unsaturated aldehydes and ketones (and related compounds) and their common reactions.
5 x 3 hour laboratory / workshop sessions. Laboratory work is sourced from the School of Chemical and Pharmaceutical Sciences Laboratory Manuals.
Students will learn through lectures, problem solving and laboratory practicals and workshops.
Self directed learning is encouraged.
Online resources to encourage pre-laboratory and pre-lecture preparation will be hosted via Brightspace.
|Module Content & Assessment