Newcastle University

Pre Requisite Comment

N/A

Co Requisite Comment

N/A

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

Intended Knowledge Outcomes

At the end of the module a student will be able to:

• understand basic principles of organic and polymer chemistry
• understand analysis of molecules and how conformation affects reactivity
• know the mechanistic rationale of substitution and elimination reactions
• understand the aromaticity and the chemistry of aromatic systems
• know the different aromatic substitution processes and their application to heteroaromatic
systems
• know the main syntheses of heteroaromatic ring systems and be able to relate these to key
concepts of carbonyl chemistry
• understand the ways in which enolates can be prepared including control of regio- and
stereochemistry
• understand the ways in which enolates react including reaction mechanisms and reagents

Intended Skill Outcomes

At the end of the module a student will be able to:

• visualise and draw three-dimensional molecules and relate sketches to the chemistry of the molecule
• propose curly arrow mechanisms using basic principles of organic chemistry
• select and develop strategies for the synthesis, purification and identification of organic and
polymeric compounds.
• solve problems of synthesis and mechanism

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.

General Notes

N/A