Module overview
Linked modules
Pre-requisite(s): (CHEM1054 and (CHEM2029 or CHEM3052 or NATS2003)) OR (CHEM1032 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.
- Accurately draw reaction mechanisms to explain or predict the course of organic reactions.
- Recognise a broad range of reactive centres in organic molecules and the types of reactions they might undergo.
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 |
|---|---|
| Wider reading or practice | 38 |
| Practical | 30 |
| Revision | 20 |
| Tutorial | 6 |
| Assessment tasks | 20 |
| Preparation for scheduled sessions | 12 |
| Lecture | 24 |
| 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% |
| Examination | 60% |
| Laboratory practicals | 30% |
Repeat Information
Repeat type: Internal & External