Reaction Mechanisms in Organic Chemistry

Learning Outcomes

Subject Specific Practical Skills

Having successfully completed this module you will be able to:

• Meet the learning outcomes of a co-requisite practical module.

Knowledge and Understanding

Having successfully completed this module, you will be able to demonstrate knowledge and understanding of:

• 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.
• Rationalise a range of substitution, rearrangement, elimination, insertion, addition and condensation reactions.

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.

Lectures (incorporating problem classes), small group tutorials (laboratory sessions in co-requisite course)

Summative

This is how we’ll formally assess what you have learned in this module.