Aims and Objectives
Having successfully completed this module you will be able to:
- skills in communicating synthetic organic chemistry
- Interpret data from a range of physical techniques to characterise Organic compounds.
- Present the results of a practical investigation in a concise manner.
- Evaluate the risks associated with an experiment and understand how to mitigate against those risks.
- Set up glassware and apparatus to conduct experiments in Organic Chemistry.
- the ability to apply such knowledge and understanding to the solution of problems related to the synthesis of organic target molecules
- the ability to demonstrate knowledge and understanding of essential facts, concepts, principles and theories relating to retrosynthetic analysis and heterocyclic chemistry
1) Retrosynthetic Analysis and the Disconnection Approach
- Introduction to retrosynthetic analysis and the disconnection approach.
- Functional Group Interconversions. Application to the synthesis of amines (amide reduction, reductive amination, nitrile, nitroalkane alkylation/reduction
- Timing of disconnections: synthesis of aromatic compounds (regioselectivity), reactions of aromatic side chains (emphasis on reversal of directing effects)
- Protecting groups (Benzyl ether, THP ether, silyl ether, acetal, phthalimide, carbamate)
- Functional Group Additions. Ester and ketone alkylation, malonate and acetoacetate chemistry. Decarboxylations.
- 1,3-disconnections. Aldol, Reformatski, (Horner-) Wittig, Knoevenagel, Mannich, Claisen, conjugate addition
- 1,5-disconnections: enolate conjugate addition
- 1,4-disconnections: Umpolung. Reactions of thioketals as an acyl anion synthon, nitro compounds
- 1,2-disconnections. Epoxide opening, pinacol and acyloin couplings, alkene dihydroxylation
- Alkene formation. Wittig reactions, alkyne reductions (synthetic applications of acetylenes)
- Ring formation methods. Dieckmann condensation, Birch reduction of aromatic rings, Robinson annelation, pinacol and acyloin couplings, Diels-Alder (brief).
2) Synthetic Manipulation of Specific Functional Groups
- Application of important methodology (aldol reactions, conjugate addition, electrophilic aromatic substitution, heterocycle synthesis)
- Application of spectroscopic methods in organic characterisation. Coupling constants in cyclohexane chair conformations, C-F and H-F couplings.
3) Aromaticity and the Chemistry of Aromatic Hetrocycles
- Structure and bonding in benzene and COT, Hückel rules, aromatic ions and introduction to aromatic heterocycles.
- Overview of the importance of aromatic heterocycles in biochemistry, technology, medicine and agriculture.
- Principles of reactivity and ring-synthesis of aromatic heterocycles.
- Pyrrole, furan and thiophene: structure, reactivity and synthesis.
- Pyrazolones and azlactones: structure, reactivity and synthesis
- Indole and benzofuran: structure, reactivity and synthesis.
- Imidazole, oxazole and thiazole: structure, reactivity and synthesis.
- Pyridine, pyridinium, quinoline and isoquinoline: structure, reactivity and synthesis.
4) NMR analysis:
- Understanding multiplicity
- Ability to measure coupling constants
- Interpretation of coupling constant values in a structural context
Learning and Teaching
Teaching and learning methods
Lectures, tutorials, problem class, workshop, practicals
Practical hours includes pre-laboratory e-learning.
Preparation for scheduled sessions hours includes other independent study.
|Preparation for scheduled sessions||57|
|Completion of assessment task||24|
|Practical classes and workshops||29|
|Total study time||150|
Resources & Reading list
J A Joule, K Mills. Heterocyclic Chemistry. Wiley.
J Clayden, N Greeves and S Warren. Organic Chemistry. Oxford: OUP.
A. Randazzo. Guide to NMR Interpretation. Editorial Loghia.
P Sykes. Guidebook to mechanism in Organic Chemisty. Editorial Longman.
S Warren. Organic Synthesis: The Disconnection Approach. Wiley.
D T Davies. Aromatic Heterocyclic Chemistry. OUP.
All absences from practical sessions must be validated and unexcused absences will result in failure of the module.
Repeat year externally: allowed if practical attendance criteria has been met. The practical marks are retained, the theory assessment is exam only.
Repeat year internally: note that practical may be reassessed by resubmission of reports or repeated.
This is how we’ll formally assess what you have learned in this module.
This is how we’ll assess you if you don’t meet the criteria to pass this module.
Repeat type: Internal & External