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2011/2 Provisional Module Catalogue - UNDER CONSTRUCTION & SUBJECT TO CHANGE
 Module Code: CHE2024 Module Title: INTERMEDIATE ORGANIC CHEMISTRY
Module Provider: Chemical Sciences Short Name: CHE2024
Level: HE2 Module Co-ordinator: CUNNINGHAM ID Dr (Chem Science)
Number of credits: 15 Number of ECTS credits: 7.5
 
Module Availability
Semester One
Assessment Pattern

Coursework  - 30%  practical write-up  (submission deadline 3 weeks 

                       after last practical session)

 

Examination  -  70%

 
Module Overview
Prerequisites/Co-requisites
Module Aims

·         To further develop the organic functional group and mechanistic chemistry introduced in level 4

 

·         To introduce C-C forming reactions and strategies, especially with respect to cyclisations

 

·         To introduce heterocyclic chemistry

To further develop the skills and practical abilities introduced in HE1 to a level appropriate to independent research
Learning Outcomes

On successful completion of this module you should be able to:

 

·         recognise the various strategies for building the carbon skeleton, particularly in the context of cyclisations

 

·           identify and explain, using simple FMO theory, Diels-Alder and Electrocyclic reactions

 

·           recognise rearrangements, and be able to apply them to synthesis

 

·           understand the chemical and physical properties of common heterocycles, particularly the structural features that influence reactivity

 

·           recognise the various strategies for building of heterocyclic frameworks

 

·           generally, be able to show the mechanisms that underlie the reactions covered

 

·           competently carry out standard organic laboratory techniques

 

·           reproduce an organic preparation following a standard written experimental procedure

 
Module Content

 

 

 

Lecture No:

 

Lecturer

 

Topic

 

 

 

 

 

 

CARBONYL CHEMISTRY

 

1-3

 

IDC

 

Aldol,& Claisen condensations, the Wittig reaction.

 

 

 

Malonic and Acetoacetic Ester syntheses, Michael addition

 

 

 

Examples of syntheses using carbonyl chemistry

 

 

 

PREPARATION OF CarbocyclicS

 

4-14

 

 

IDC

 

 

Cyclisation by intramolecular nucleophilic addition: General considerations, Diketone synthesis, Dieckmann cyclisation, Thorpe-Ziegler reaction, Michael reaction

 

 

 

Reductive cyclisation:     Acyloin condensation, Pinacol reactions

 

 

 

Acid catalysed cyclisation: Dienes

 

 

 

Cyclisations using Enamines: Stork reaction

 

 

 

Diels Alder reactions and Introduction to Frontier Molecular orbital theory; Some examples of syntheses using Diels Alder reactions

 

 

 

Electrocyclic reactions, thermal/photochemical reactions, disrotatory, conrotatory,

 

 

 

Further FMO theory

 

 

 

Carbene Chemistry

 

 

 

Preparation of carbocyclic compounds from carbocyclic precursors: Reduction of aromatic system: Birch reduction

 

 

 

Ring contractions: Favorski reaction, Benzilic acid rearrangement

 

 

 

Ring expansions: Baeyer-Villiger reaction, Beckmann rearrangement

 

 

 

HETEROCYCLIC CHEMISTRY

 

15-25

 

IDC

 

Heterocycles: relevant examples, nomenclature

 

 

 

The chemistry of pyridine: synthesis, structure and properties

 

 

 

General reactivity of pyridines

 

 

 

Quinoline and isoquinoline: synthesis, structure and properties

 

 

 

General reactivity of quinolines and isoquinolines

 

 

 

Pyrrole, furan and thiophene: synthesis, structure and properties

 

 

 

General reactivity of pyrroles

 

 

 

General reactivity of furans and thiophenes

 

 

 

Problem-solving sessions

 

 

 

 

 

 

PRACTICAL ORGANIC CHEMISTRY

 

Various

 

38 hours

 

 

 

The Beckmann Rearrangement

 

Crossed Aldol Condensation

 

The Grignard Reaction

 

Diels-Alder Reaction

 

Heterocyclic compound preparation

 

Epoxidation of 3,5,5-trimethylcyclohex-2-en-1-one

 
Methods of Teaching/Learning
Formal lecture and practical sessions
Selected Texts/Journals

Recommended
Bruice, P. Y. (2011) Organic Chemistry, Upper Saddle River , Pearson.

 

Clayden, J., Greeves, N., Warren, S.; Wothers, P.: (2001) Organic Chemistry  Oxford, Oxford University Press.

 

Joule, J.; Mills, K.: (2010) Heterocyclic Chemistry, Chichester , Wiley.

 

Suggested

 

Fleming, I. (2009) Molecular orbitals and organic chemical reactions, Chichester , Wiley.

 

Sykes, P. (1986) Guidebook to Mechanism in Organic Chemistry, Pearson/Prentice Hall.

 

Sykes, P. (1995) A Primer to Mechanism In Organic Chemistry, Pearson/Prentice Hall.
Last Updated

21 April 2011