Aims

To provide a thorough understanding of the influence of conformational and stereoelectronic effects on the reactivity of organic compounds; to show how mechanisms of some organic reactions have been investigated and to present the currently accepted mechanisms of these reactions; to provide an understanding of mechanistic and synthetic chemistry; to consider the chemistry of aromatic systems; to provide an understanding of polymer characterization and methods of characterization; to understand fundamental mechanistic differences between step-growth and chain growth polymerizations; to show how the most commonly utilised classes of polymers are synthesized and to outline their properties.

Outline Of Syllabus

Aromatic Chemistry including Rearrangements

The definitions of aromaticity
Electrophilic aromatic substitution
Electrophilic aromatic substitution reactions of substituted benzenes
Synthesis of substituted benzenes; the reactions of benzene diazonium salts
Nucleophilic aromatic substitution; the chemistry of benzyne
Aromatic oxidations and reductions
Rearrangement reactions

Enolate chemistry

Formation of enolates and pKa
Enolate alkylation; O vs C alkylation, kinetic vs thermodynamic control, 1,3-dicarbonyls and the use
of malonates in synthesis
The aldol reaction; aldol, dehydration of products, intramolecular aldol and cross aldol
Acylation of enolates; Claisen and Dieckmann condensations
Tandem processes; Darzens, Baylis Hillman, Robinson etc.
Enamines; formation and reactions

Stereochemistry and Mechanism

Stereochemistry. Revision of basic concepts.
Conformations of acyclic compounds.
Conformations of 3-6 membered rings
Higher energy conformations of cyclohexanes
Stereocentres at atoms other than carbon. Chiral molecules which do not contain a stereocentre.
Topism
Investigating reaction mechanisms
Hammett relationships

Polymer Chemistry

What are polymers;
Polymer molecular weights and molecular weight distributions;
Step-growth and chain growth polymerizations;
Synthesis of commonly used polymers;
Properties of polymers;
Recycling polymers;
Biopolymers

Teaching Rationale And Relationship

The important basic principles of organic chemistry introduced in Stage 1 will be reinforced and built on by material covered in the lectures. This will be supported by tutorials that will allow small groups of students to tackle an array of different problems associated with the lecture material and help prepare for the assessment.

Assessment Rationale And Relationship

The summative written examination will assess the level of knowledge and understanding of all aspects of the module. The examination will present students with questions from a selection of topics learnt throughout semester 1 and 2 module content.

Formative assessment will allow students to gain feedback during the module.