CHEM61041 Organic Chemistry

 

Unit code: CHEM61041
Credit Rating: 15
Unit level: Level 6
Teaching period(s): Semester 1
Offered by School of Chemistry

Aims

The expansion and exercise of the student’s knowledge of the fundamentals of organic chemistry

Overview

Designing Organic Syntheses: The Chemistry of Bifunctional Organic Compounds: (Dr A C Regan, 8 lectures)

  • Enolate formation, alkylation and aldol reactions
  • Synthesis of 1,3-dicarbonyl compounds (Claisen and Dieckmann condensations) - enolization, alkylation, decarboxylation
  • Use of malonate and acetoacetate in organic synthesis – comparison with the chemistry of simple enolates
  • Preparation, properties and use of α,β-unsaturated carbonyl compounds in synthesis (Michael and Robinson reactions)
  • Disconnections of target molecules containing two functional groups – 1,3-difunctionals, α,β -unsaturated carbonyl and 1,5-difunctional compounds. These will be discussed throughout the above topics, where appropriate
  • Disconnections of 1,2- 1,4- and 1,6-difunctional compounds

Modern Physical Organic Chemistry: (Dr J Bures, 8 lectures)

  • The relationship between free energy change, equilibrium constant and reactivity
  • The physical concepts necessary for the design of experiments to test or establish a reaction mechanism, and the application of physical methods to mechanistic problems
  • The effects of structural variation and change of reaction conditions on organic reactivity
  • Types of supramolecular interactions and their relative strengths
  • Some applications of supramolecular chemistry

Heterocycle Synthesis: (Dr J M Gardiner, 8 lectures)

  • Main classes of 5- and 6-membered heterocyclic compounds containing one heteratom
  • Importance of heterocycles (eg drugs, natural products, materials) will be highlighted throughout.
  • Retrosynthetic analysis of heterocyclic targets – each class and reaction type
  • Synthetic methods for synthesis of 5-membered and 6-membered ring aromatic heterocycles (pyrroles, furans, indoles), illustrating throughout classical applications using condensation reactions, (amine-carbonyl, 1,3-,1,4 and 1.5-dicarbonyls, other active methylenes) and Michael reactions (using a range of different nucleophile types) with an emphasis on mechanistic understanding and common reaction-type themes in hetereocyclic construction:
    • A1 Pyrroles: Paal-Knorr, Knorr, Hantzsch, glycine ester, Kenner and isocyanides
    • A2 Furans: 1,2-, 1,3- and 1,4-dicarbonyl based approaches, and Diels-Alder.
    • A3 Pyridines: Hantsch and variants
    • B1 Indoles: Sigmatropics (Fisher, Bartoli, Gassman), Bishler, Madelung, Reissert and Nenitzescu
    • B2/B3 Quinolines and Isoquinolines: Skraup/Doebner-Miller, Combes, Knorr-like, Friedlander and Bischler-Napieralski, Pictet-Gams/Spengler, Pomeranz-Fritsch

Learning outcomes

 Students successfully completing this unit should:

  • Have an understanding of the chemistry of bifunctional organic compounds, and how they can be used in synthesis
  • Have an appreciation of how the mechanisms of organic reactions are described and determined
  • Have an appreciation of how mechanism are used in other branches of organic chemistry
  • Understand classical strategies for heterocyclic synthesis and devise and explain syntheses of aromatic heterocycles
  • Have an appreciation of mechanisms of heterocyclic syntheses

Transferable skills and personal qualities

  • Problem-solving skills
  • Numeracy and mathematical skills
  • Investigative skills
  • Analytical skills
  • Time management and organisational skills

Study hours

  • Lectures - 24 hours
  • Tutorials - 3 hours
  • Lab work – 18 hours
  • Independent study hours - 95 hours
  • Revision session – 2 hours
  • Assessed coursework  – 5 hours
  • Assessment written exam – 2.5 hours

Assessment methods

  • Written exam - 70%
  • Laboratory and practical coursework - 25%
  • Coursework in retrosynthetic analysis - 5%

Recommended reading 

  1. Organic Chemistry J Clayden, N Greeves, S Warren and P Wothers (Oxford University Press, 2001) ISBN 0198503466
  2. Organic Synthesis: the Disconnection Approach, S Warren and P Wyatt, 2nd edition, Wiley, 2008. ISBN 9780470712368
  3. The Physical Basis of Organic Chemistry. H. Maskill, OUP, 1985. ISBN 9780198551997
  4. Modern Physical Organic Chemistry E V Anslyn and D A Dougherty (University Science Books, 2006) ISBN 9781891389319
  5. Supramolecular Chemistry J W Steed and J L Atwood (Wiley, 2000) ISBN 0471987918
  6. Supramolecular Chemistry, P Beer, P Gale and D K Smith, OUP, 1999. ISBN 9780198504474
  7. Heterocyclic Chemistry, J A Joule, K Mills, Blackwell, 2010. ISBN 978-0632054534
  8. Aromatic Heterocyclic Chemistry, S G Davies, OUP, 1992. ISBN 978-0198556602

Feedback methods

Core tutorials and individual feedback from tutors/lecturers.

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