Module overview
Linked modules
Pre-requisites: (CHEM1054 and (CHEM2029 or CHEM3052 or NATS2003))
Aims and Objectives
Learning Outcomes
Knowledge and Understanding
Having successfully completed this module, you will be able to demonstrate knowledge and understanding of:
- Rationalise a range of substitution, rearrangement, elimination, insertion, addition and condensation reactions.
- Recognise a broad range of reactive centres in organic molecules and the types of reactions they might undergo.
- Accurately draw reaction mechanisms to explain or predict the course of organic reactions.
Subject Specific Practical Skills
Having successfully completed this module you will be able to:
- Meet the learning outcomes of a co-requisite practical module.
Syllabus
Revision of SN1 and SN2 mechanisms; Stability of Carbenium ions; Dipolar aprotic solvents; Nucleophilicity vs basicity; Neighbouring Group Participation; Use of isotopic labelling; Rearrangements; Carbenium ions - Wagner Meerwein, Pinacol, Semi-pinacol; Migration to oxygen and nitrogen - Baeyer-Villiger , Beckmann; Anion driven - Benzoic acid, semi-benzoic acid, Favorski.
Revision of E1 and E2 Eliminations; Kinetic isotope effect; Carbenes - Cyclopropanation, C-H insertions and rearrangements; Radicals - Stability and structure. Formation and reactions.
Electrophilic addition to alkenes and dienes; Electrophilic aromatic substitution; Carbanion structure, stability and formation; Enolisation and enolate formation, including basicity and pKa(H); Aldol addition and condensation (self and crossed), including E1cb;
Claisen and Dieckmann condensation; Knoevenagal.
Enolate alkylation; Silyl enol ethers; Conjugate addition; Nucleophilic aromatic substitution.
Learning and Teaching
Teaching and learning methods
Lectures (incorporating problem classes), small group tutorials (laboratory sessions in co-requisite course)
| Type | Hours |
|---|---|
| Tutorial | 6 |
| Preparation for scheduled sessions | 12 |
| Practical | 30 |
| Revision | 20 |
| Assessment tasks | 20 |
| Lecture | 24 |
| Wider reading or practice | 38 |
| Total study time | 150 |
Resources & Reading list
Textbooks
J. Clayden, N. Greeves, S. Warren (2012). Organic Chemistry.
Assessment
Assessment strategy
Final exam, tutorials and laboratory marks. The latter are accumulated under the co-requisite lab module.
Summative
This is how we’ll formally assess what you have learned in this module.
| Method | Percentage contribution |
|---|---|
| Assessed Tutorials | 10% |
| Laboratory practicals | 30% |
| Examination | 60% |
Repeat Information
Repeat type: Internal & External