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- UCAS institution code
Year of entry: 2022
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Course unit details:
Core Chemistry 1
|Unit level||Level 3|
|Teaching period(s)||Semester 1|
|Offered by||Department of Chemistry|
|Available as a free choice unit?||No|
This course unit detail provides the framework for delivery in 21/22 and may be subject to change due to any additional Covid-19 impact.
Stereoselective Synthesis (Dr Nathan Owston, 8 lectures)
1. Diastereoselectivity in ring systems: conformational analysis and stereoelectronics
2. Diastereoselectivity in acyclic systems
Reactions at C=O: Prochirality, Felkin-Anh model, Chelation control
Reactions at C=C: Houk model
Reactions of enolates: alkylation and aldol reactions, cyclic transition states
Diastereoselective reactions in synthesis: production of single enantiomers
3. Asymmetric synthesis
Chiral pool approaches
Chiral auxiliaries (alkylation/aldol reactions)
4. Introduction to Asymmetric Catalysis
Catalysis with transition metals (asymmetric reduction of ketones)
Organocatalysis (asymmetric conjugate addition)
5. Applications of stereoselective reactions in synthesis (fine chemicals, pharmaceuticals)
Reactive Intermediates (Dr Roger Whitehead, 8 lectures)
Neutral reactive intermediates
Carbenes, Nitrenes, Arynes
What are radicals?
The structure of carbon-centred radicals
The relative stability of different radical species
Historical aspects of radical chemistry
Sources of radical intermediates
Radical reactions in synthesis
Solving unseen problems involving radical intermediates
Pericyclic Reactions (Dr Daniele Leonori, 8 lectures)
Frontier molecular orbitals (FMOs)
2. The Diels-Alder [4¿ + 2¿] cycloaddition reaction
FMO interactionsStereoselectivity and regioselectivity
3. Other cycloaddition reactions
[2 + 2] Processes ('forbidden' and 'allowed' variants)
Other (4n + 2) and 4n pairings
4. Selection rules and orbital symmetry
5. Electrocyclic reactions
Introduction to electrocyclic reactions
Conservation of orbital symmetry in the ring-opening of cyclobutene
6. Sigmatropic rearrangements
[1,5] and [1,7] Hydrogen shifts
[1,3] Sigmatropic shifts
[3,3] Sigmatropic rearrangements
Cope and Claisen rearrangements
|Unit title||Unit code||Requirement type||Description|
|Structure and reactivity of organic molecules||CHEM20412||Pre-Requisite||Compulsory|
The unit aims to develop further understanding of synthetic and mechanistic organic chemistry with emphasis on reactive intermediates and elements of stereochemistry.
On successful completion of the course students should be able to:
- Apply knowledge of molecular structure, reactivity and stereochemistry to both rationalise and predict the stereochemical outcome of chemical reactions
- Evaluate and propose strategies for the synthesis of complex molecules which include stereoselective reactions.
- Describe the various types of reactive intermediates that are of importance in organic chemistry and explain the physical properties and chemical reactivity of such species;
- Describe the factors that influence the structure, stability and reactivity of different radical species and explain the outcome of important reaction processes;
- Describe the various reaction types undergone by synthetically useful free radicals;
- Predict and rationalise the outcome of unseen transformations involving reactive intermediates;
- Understand the fundamental of molecular orbital analysis in pericyclic reactions;
- Be able to rationalise the stereochemical outcome of pericyclic reactions;
Teaching and learning methods
Transferable skills and personal qualities
Enhance transferable skills in the areas of problem solving and analysis
Example classes and individual feedback from tutors/lecturers
• C.J.Moody and G.H.Whitham, Reactive Intermediates (An Oxford Chemistry Primer) ISBN: 978-0-198-55672-5
• A.F.Parsons, An Introduction to Free Radical Chemistry (Wiley-Blackwell, 2000) ISBN: 978-0-632-05292-9
• J. Clayden, N. Greeves, S. Warren and P. Wothers, Organic Chemistry (Oxford University Press, 2001) ISBN 0198503466 (Chapters 35 and 36).
• J. Clayden, N. Greeves and S. Warren, Organic Chemistry 2nd edition (Oxford University Press, 2012) ISBN 0199270295 (Chapters 34 and 35).
• I. Fleming, Pericyclic Reactions (Oxford Chemistry Primer, 2nd Edition) (Oxford University Press, 2015) ISBN 0199680900 (affordable, thorough guidebook).
• I. Fleming, Molecular Orbitals and Organic Chemical Reactions: Student Edition (Wiley-Blackwell, 2009) ISBN 0470746599 (a comprehensive reference text).
• G. Procter, Stereoselectivity in Organic Synthesis (Oxford Chemistry Primers) (Oxford University Press, 1998) ISBN 978-0198559573.
• Access to a set of Orbit molecular models is essential.
|Scheduled activity hours|
|Assessment written exam||2|
|Practical classes & workshops||3|
|Independent study hours|
|Daniele Leonori||Unit coordinator|