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Module Title |
Organic Chemistry
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Module Code |
CS307
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School |
School of Chemical Sciences
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Online Module Resources
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| Module Co-ordinator | Dr Nick Gathergood | Office Number | X126 |
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Level |
3
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Credit Rating |
5
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Pre-requisite |
None
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Co-requisite |
None
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Module Aims
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To impart to the student the importance of three-dimensional thought in Chemistry. The module will concentrate on reactive intermediates with emphasis on their generation, detection and synthetic utility. The concept of reagent and substrate controlled stereochemistry in asymmetric synthesis will be introduced to the students.
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Learning Outcomes
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Students should be able to:
- Understand the concept of reactivity with respect to intermediates
- Identify well-known reactive intermediates
- Appreciate the utility of reactive intermediates.
- Understand the concept of selectivity in reaction pathways
The student should have a:
- Grasp and understanding of the reaction that the classes of compound listed under Indicative Syllabus.
- Realisation that three dimensional thought is of utmost importance in chemistry.
- Ability to design regio- and stereoselective syntheses.
- Good knowledge of reactions used to form C-C bonds.
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Indicative Time Allowances
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Hours
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Lectures |
33
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Tutorials |
3
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Laboratories |
0
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Seminars |
0
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Independent Learning Time |
39
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Total |
75
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Placements |
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Assignments |
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NOTE
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Assume that a 5 credit module load represents approximately 75 hours' work, which includes all teaching, in-course assignments, laboratory work or other specialised training and an estimated private learning time associated with the module.
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Indicative Syllabus
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1.REACTIVE INTERMEDIATES:Introduction to reactive intermediates. Free radicals: production, stability, conformations, solvent effects, abstraction, addition reactions, rearrangements. Radicals in synthesis: alkane halogenations, radical oxidations. Carbenes and nitrenes, preparation and their reactions, electronic structure, singlet vs. triplet.Arynes: generation, structure, reaction with nucleophiles, cycloadditions.Carbenes: generation, structures, triplet vs. singlet carbenes, reactions1,3-Dipoles: generation, structures, cycloaddition reactions, stereospecificity of reactions. Synthesis and reactions of phosphorous and sulfur ylides. Wittig reaction and modifications.2. Molecular re-arrangements: C to C migrations. Migratory aptitudes, anchimeric assistance and neighbouring group participation. Pinacol and related rearrangements3. Aromatic heterocyclic chemistry: pi-excessive and pi deficient rings, synthesis of heterocyclic compounds, (pyridine, pyrene, furan, thiophone, indole, quinoline, isoquinoline). Reactions of heterocycles with nucleophiles and electrophiles.4. Asymmetric SynthesisIntroduction: What is asymmetric synthesis? How to control selectivity?Part A: C-C bond formation.Nucleophilic addition to carbonyl compounds: Substrate control and Reagent control. Cram''''s model, Felkin-Anh model, Stereoselectivity of enolate formation. Alkylation of enolates. The aldol reaction. Chiral Auxiliaries. Asymmetric Aldol reaction. Nucleophilic addition to imine compounds. Mannich Reaction. Asymmetric Friedel Crafts.Part B: Asymmetric reduction. Organoboranes, hydrogenation (substrate control) Part C: Asymmetric addition to C=C. Hydroboration, Hydrosilyation, Epoxidation, Aziridination, Dihydroxylation, Hydroamination.
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| Assessment | | Continuous Assessment | 0% | Examination Weight | 100% |
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Indicative Reading List
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Essential:Advanced Organic Chemistry J. March (Wiley Interscience)Reactive Intermediates, C.J. Moody and G.H. Whitham, Oxford University Primers.Supplementary:Organic Reactions and Orbital Symmetry, T.Gilchrist and R.Storr, Cambridge University PressCarbenes, Nitrenes and Arynes, T. Gilchrist and C.W.ReesFree Radical Chain Reactions in Organic Synthesis, Cambridge University Press.Radicals in Organic Synthesis: Formation of Carbon-Carbon bonds, Pergammon PressElementary organic Stereochemistry and Conformational Analysis, B.A. Marples, RSC. Selectivity in Organic Chemistry, R. S. Ward, (Wiley)Stereochemistry of Organic Compounds, E. L. Eliel and S. H. Wilen, (Wiley Interscience)
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Programme or List of Programmes
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| AC | BSc in Chemical and Pharmaceutical Sc. |
| BSSA | Study Abroad (DCU Business School) |
| BSSAO | Study Abroad (DCU Business School) |
| ECSA | Study Abroad (Engineering & Computing) |
| ECSAO | Study Abroad (Engineering & Computing) |
| HMSA | Study Abroad (Humanities & Soc Science) |
| HMSAO | Study Abroad (Humanities & Soc Science) |
| SHSA | Study Abroad (Science & Health) |
| SHSAO | Study Abroad (Science & Health) |
| Archives: | |
