Advanced Organic Chemistry 1 (Stereochemistry and Mechanisms)

Module summary

Module code: CHEM1102
Level: 6
Credits: 15
School: Engineering and Science
Department: Science
Module Coordinator(s): Adrian Dobbs

Specification

Pre and co requisites

CHEM1030; CHEM1034.

Aims

To extend student knowledge of mechanistic organic chemistry.
• To provide students with a fundamental understanding of the relationships between molecular structure and reaction mechanism.
• To enable students to apply frontier molecular orbital theory to pericyclic, free radical, nucleophilic substitution/addition reactions.
• To provide students with an understanding of linear free energy relationships and the use of Hammett plots in predicting reaction rates/investigating reaction mechanisms.
• To introduce students to reactive intermediates (radicals, arynes, carbenes/nitrenes).
• To introduce students to asymmetric synthesis.

Learning outcomes

On successful completion of this module a student will be able to:
1. Use of physical chemistry parameters in determining reactions mechanisms; kinetic isoptpe effects; LFER plots to predict reaction rates and elucidate reaction mechanisms.
2. Describe the key frontier orbital interactions that are involved in typical pericyclic, free radical and nucleophilic addition substitution reactions
3. Appreciate the importance and challenges in asymmetric synthesis, exemplified by Felkin-Anh and chelation models and asymmetric aldol reactions.

Indicative content

1. Physical organic chemistry: kinetics & thermodynamic effects; Hammond postulate; Curtin-Hammett principle; LFER; KIE.
2. Pericyclic Reactions: orbitals; reactions of conjugated systems: cycloaddition reactions; electrocyclic reactions; sigmatropic rearrangements; cheleotropic reactions.
3. Reactive intermediates: arynes; radicals; carbenes and nitrenes.
4. Introduction to asymmetric synthesis: Felkin-Anh and chelation control in carbonyl reactions; asymmetric aldol reactions.