Further Organic Chemistry

Module summary

Module code: CHEM1034
Level: 5
Credits: 15
School: Engineering and Science
Department: Science
Module Coordinator(s): Adrian Dobbs

Specification

Aims

This module develops and enhances the knowledge of organic chemistry gained in the Level 4 module Organic Chemistry, which underpins both the industrial chemistry and the biological applications of organic molecules. It underpins an in-depth study of the chemistry of carbon compounds from the viewpoint of their synthesis, reactions and mechanisms. The relevance of atomic structure, stereochemistry and functional group chemistry is also developed further to unify the underlying chemistry.

Learning outcomes

On successful completion of this module a student will be able to:
1. Analyse the structures and conformations of organic molecules and the properties and reactions of optically active molecules.
2. Describe the physical and electronic structures of aromatic, carbonyl and heterocyclic compounds.
3. Design and use reactions of aromatic and heteroaromatic compounds in organic synthesis
4. Design synthetic routes using the reactions of carbonyl compounds.
5. Work independently in the laboratory and clearly report experimental procedures, results and conclusions.

Indicative content

1. Structure, bonding and stereochemistry
Structure and bonding in organic molecules; orbitals.
Conformationational analysis: alkanes; small, normal and large rings. Conformations:3-6 membered rings, axial and equatorial substituents , conformational equilibria.
Chirality: molecules containing chiral carbon atoms, optical activity, chiral molecules without asymmetric carbon atoms, racemic mixtures, enantiomerism, chemical and chromatographic resolution and separation of enantiomers, physical properties of diastereoisomers. Representations of sterochemistry: use of molecular models to demonstrate the stereochemical nature of molecules, Fischer and Newman projections, use of sequence rules to assign R/S configuration
Stereochemistry of chemical reactions: examples of retention of configuration, racemisation, retention of configuration, asymmetric synthesis.

2. Aromatic compounds
The structure of benzene: physical structure, methods of representation, bonding, conjugation, resonance, aromaticity, energy of benzene.
Aromatic hydrocarbons: benzenoid and non-benzenoid aromaticity, energy diagrams, the Huckel Rule, 2, 4, 6 and 8 systems, polynuclear benzenoid hydrocarbons.
Aromatic heterocycles: pyridine, pyrrole, furan, thiophene.
Electrophilic substitution: nitration, bromination and sulphonation of benzene, effects of activating and de-activating substituents, mechanisms of reactions, influence on design of syntheses, Friedel-Craft alkylation and acylation. Unique reactions of functional groups on aromatic rings.
Nucleophilic aromatic substitution: ring activation, typical leaving groups, addition-elimination and elimination-addition mechanisms, influence on design of syntheses.

3. Reactions of carbonyl compounds
Nucleophilic addition: reactions with Grignard reagents etc.
Tautomerism: keto-enol tautomerism, acid and base catalysis, -substitution of carbonyl compounds, alkylation of enolate ions, applications in synthesis.
Condensation reactions: Aldol condensation; base and acid catalysis, dehydration of products, intramolecular and crossed-aldol reactions; formation of ethyl acetoaceate, properties, uses in synthesis; malonic esters as synthetic starting materials.
Conjugate additions: reactions of unsaturated compounds, Michael addition and Robinson annulation reactions.

4. Heteroaromatic chemistry
Introduction to pyridine, pyrrole, furan and thiophene: structure and reactions.