module specification

This module relates the physical and chemical behaviour of polyfunctional cyclic organic compounds and biomolecules to their structures and electronic properties. Taught classes will be reinforced by practical exercises and spectroscopic problems.

CY4061

Available for Study Abroad? YES

Alicyclic chemistry - effect of ring size on the stability of alicyclic compounds; types and causes of strain. Methods for the synthesis of alicyclic compounds with rings of 3-20 carbon atoms: intramolecular carbanion condensation reactions, the acyloin and related reactions. Conformation in alicyclic compounds and carbohydrates: effects of conformation on rate and outcome of reactions in cyclohexane derivatives; differences between reactions of alicyclic compounds and their acyclic counterparts.

The chemistry of aromatic ring systems; electrophilic and nucleophilic substitution reactions. Heterocyclic aromatic systems 5- and 6-membered rings.

Simple MO theory: thermal and excited state reactions of conjugated π-systems. Ethene, butadiene, hexatriene: electrocyclic reactions, the Diels-Alder and higher order cycloadditions (LO 1-3)

Spectroscopic characterisation of organic compounds: use of NMR in structure elucidation of complex systems: 1H decoupled spectra, 1H-1H and 1H-13C correlation spectra (LO 4).

Teaching and learning sessions include lectures//workshops, tutorials, practical classes with feedback where appropriate.

Tutorials have an emphasis on problem solving based on pre-set work with student participation and group activities. Students will be expected to prepare in advance for tutorials to develop problem-solving skills using worksheets provided. Feedback from these sessions facilitates the learning process. Lectures are used to set context and to deliver subject material, and are linked to tutorials, the practical and problem sessions. Students will be expected to reflect on the learning experience and develop their own understanding of the material.

On successful completion of this module the student will be able to:

1. Apply simple LCAO and MO theory to predicting the outcome of reactions involving molecules containing conjugated π-systems;
2. Recognise the conformational limitations placed on cyclic structures and thus explain differences in their chemical behaviour with those of their aliphatic counterparts;
3. Perform selected synthetic and purification techniques, and relate to the lecture material.
4. Interpret 1H, 13C, and 1H-13C correlation NMR spectra in elucidation of structures of polyfunctional organic compounds.

This module will be assessed by a 20-minute powerpoint presentation, and an end of semester exam.

A 20-minute powerpoint presentation (50%) will assess the students’ ability to independently research an organic chemistry reaction of their choice, which was not covered in the lectures. They will need to demonstrate clearly that they have understood the detailed mechanisms involved and give examples of where the reaction has been applied, e.g., to the synthesis of a modern pharmaceutical, or a complex natural product.
Contributions to organic chemistry by BAME researchers will be particularly emphasised, and the students will need to reflect on a podcast that questions whether reactions should be named after the chemists who first reported them.

An end-of-module examination (50%) will assess the students’ knowledge of organic reaction mechanisms, practical procedures and spectroscopic characterisation. Students will be required to draw on relevant material delivered throughout the course to predict and explain specific outcomes of hitherto unseen reactions.

To pass the module students must achieve a minimum aggregate mark of 40%. There will be an attendance requirement for the practical sessions. If the module is passed on reassessment, then the maximum mark awarded will be 40%.

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