1. Compare, contrast and critically evaluate methodologies for C-C bond formation, reaction group introduction and interconversion, and cyclisation reactions using classical and topical examples KNOWLEDGE AND UNDERSTANDING
LEARNING

2. Apply the Disconnection Approach to the multi-step synthesis of a complex organic molecule ANALYSIS
APPLICATION

3.Demonstrate an increased level of practical ability in the synthesis and characterisation of complex organic molecules
SS2

4. Show an advanced level of ability in communication of scientific results
COMMUNICATION
ANALYSIS

Students will study the formation of C-C bonds through a variety of classical and topical methodologies. The use of carbanions, including the formation of organilithium and organomagnesium compounds, and the reactions of these species, such as alkylation, transmetallation, transition-metal-catalysed cross-coupling, will be discussed.

Also, the formation of C-C bonds using radicals, including an introduction to this area of chemistry will be discussed, leading onto intermolecular additions, intramolecular cyclisations and tandem and cascade processes. Baldwin’s guidelines for cyclisation reactions will be introduced.

Pericyclic addition reactions, including Diels-Alder-, 1,3-diploar and related cycloadditions, concerted electrocyclic ring opening and closure reactions (stereochemistry), and sigmatropic rearrangements will be discussed, building an appreciation of how the frontier molecular orbitals involved in the reactions allows prediction of reaction outcome, rates, regio- and stereochemistry.

Students will learn about the synthetic manipulation of specific functional groups, including aldol reactions, conjugate additions, electrophilic aromatic substitution and heterocycle synthesis.

Students will also develop their abilities to use spectroscopic methods for characterisation of organic molecules. In particular, the practical application and interpretation of NMR spectra will provide insight into the structural and conformational nature of molecules encountered in classes and synthesised during laboratory exercises.

Retrosynthetic analysis and the Disconnection Approach will be introduced to give students a methodology for development of reaction schemes leading to a proposed target molecule. This will include the sequencing of reaction steps, use of protecting groups, functional group interconversions and additions, alkene formations, ring formation methods, and conjugate disconnections.

Laboratory exercises will provide students with the opportunity to undertake a complex multi-stage synthesis, including the use of a variety of purification methods, and carry out characterisation using NMR and other spectroscopic methodologies.

Students will complete 3 elements of assessment for this module:

1. EXAMINATION 1 (at the end of Semester 1), 2 hour worth 25% of the module (learning outcomes 1and 2)

2. PRACTICAL PORTFOLIO, worth 50% of the module (learning outcomes 2, 3 and 4)

This will include a laboratory notebook, written reports of experiments, a reflective summary of knowledge and skills development (learning outcome 3)

3. EXAMINATION 2 (at the end of semester 2), 2 hour worth 25% of the module – FINAL (learning outcomes 1and 2)

4. Formative assessment: Students will be provided with formative assessment and feedback via practical classes, reports, and tutorial sessions and specimen exam/test questions. (all learning outcomes)

Each week there will be a 2-hour interactive lecture / seminar during which students will be introduced to core material and develop their understanding through problem-solving exercises undertaken in class = 48 hours.

There will be 16 x 3 hour practical sessions during which students will develop their practical and experimental skills through undertaking a number of laboratory-based exercises that also develop the theoretical aspects of the module = 48 hours.

Each experiment is preceded by a pre-laboratory exercise that involves a combination of audio visual resources, accessible via Blackboard, that helps students prepare for the practical work, with a short formative quiz based on the content to be completed before starting the relevant practical task. It is anticipated that students will spend 2 hours on each of these activities = 32 hours.

The remaining 172 hours of independent study will be used to research background information related to the delivery of the core material and to build the practical portfolio.

Housecroft and Constable (2010), Chemistry,4th Ed, Prentice Hall

Clayden, Greeves and Warren (2012), Organic Chemistry, 2nd Ed, OUP Oxford

Levy (2017), Arrow-Pushing in Organic Chemistry, 2ed Ed, Wiley