CH3O2: Advanced Organic Chemistry - Contemporary Synthetic Methodology

Module Provider:

Chemistry, School of Chem, FoodBi and Pharm

Number of credits:

10 [5 ECTS credits]

Level:

H (Honours)

Terms in which taught:

Spring

Module Convenor:

Dr JB Sweeney

Pre-requisites:

CH2O1

Co-requisites:

Modules excluded:

Module version for:

2007/8

Aims:
The course aims to relate advanced topics in organic chemistry to subject areas covered in previous modules and provide a foundation of knowledge to enable a better understanding of the primary chemical literature.

Assessable learning outcomes:
Students who have successfully completed this module will be able to:

Additional outcomes:
Through the provision of lectures and tutorials students will develop a broader appreciation of the expansive nature of modern synthetic organic chemistry. The ability of each student to understand and apply this knowledge will be developed via a number of small group tutorials.

Outline content:
J B Sweeney (6 lectures) Advanced Organometallic Chemistry
Principles and special features of reactions catalysed by transition metal complexes. The course will focus on cyclisation reactions and the Suzuki, Heck and Stille reactions.
L M Harwood (7 lectures) Orbital Symmetry
Electrocyclisations, sigmatropic rearrangements, cheletropic rearrangements and cycloadditions. Frontier molecular orbital rules for stereochemical and regiochemical prediction. Woodward-Hoffman rules and Huckel-Möbius interactions. Reactions covered will include [2+2], [3+2] and [4+2] cycloadditions including the Diels-Alder reaction, [3.3] sigmatropic rearrangements including the Claisen and Cope reactions and [1.3], [1.5], [1.7] hydride and alkyl shifts.
J E Mckendrick (6 lectures) Radical Reactions in Synthesis
The properties and use of free radicals in synthesis will be discussed. Areas covered will include radical addition reactions, radical cyclisations, tandem radical reactions, the acyloin reaction and the Birch reduction.
L M Harwood (5 lectures) Advanced Organic Synthesis and Retrosynthetic Analysis
Strategies involved in the construction of complex natural products. The central role of the carbonyl group in retrosynthetic analysis will be reviewed. The synthesis of a range of structurally complex molecules will be described.

Brief description of teaching and learning methods:
Two one hour lectures per week with approximately one tutorial on related material every two weeks.

Contact hours:

Assessment:
Coursework
Students will attend tutorials on the material covered in this module. Attendance is compulsory. A tutorial comprises both written work and oral contribution.
For students on chemistry-based degree courses any unexplained absence from more than two tutorials in chemistry in any term will automatically incur a formal warning from the School Director of Teaching and Learning.
Examinations
A one and a half hour paper taken during the Part 3 examination period. 100%
Requirements for a pass
A mark of 40% .
Reassessment arrangements
Re-examination will take place in the September following final examinations, for the examinable component only, when a student has failed the programme overall.