Registry

Module Specifications

Current Academic Year 2012 - 2013
Please note that this information is subject to change.

Module Title	Organic Chemistry
Module Code	CS307
School	School of Chemical Sciences
Online Module Resources
Module Co-ordinator	Semester 1: Nick Gathergood Semester 2: Nick Gathergood Autumn: Nick Gathergood
Module Teacher	Nick Gathergood
NFQ level	8	Credit Rating	5
Pre-requisite	None
Co-requisite	None
Compatibles	None
Incompatibles	None

Description

To impart to the student the importance of three-dimensional thought in Chemistry. The module will concentrate on reactive intermediates with emphasis on their generation, detection and synthetic utility. The concept of reagent and substrate controlled stereochemistry in asymmetric synthesis will be introduced to the students.

Learning Outcomes

1. Demonstrate the concept of reactivity with respect to intermediates
2. Identify well-known reactive intermediates
3. Appreciate the utility of reactive intermediates.
4. Show the role of the concept of selectivity in reaction pathways
5. Demonstrate the reactions that the classes of compound listed under Indicative Syllabus
6. Apply concept of 3D structure to reactions under indicative syllabus
7. Ability to design regio- and stereoselective syntheses
8. Demonstrate knowledge of reactions used to form C-C bonds.

Workload	Full-time hours per semester
*Type*	*Hours*	*Description*
Lecture	36	No Description
Independent learning	89	No Description
Total Workload: 125

All module information is indicative and subject to change. For further information,students are advised to refer to the University's Marks and Standards and Programme Specific Regulations at: http://www.dcu.ie/registry/examinations/index.shtml

Indicative Content and Learning Activities

REACTIVE INTERMEDIATES.
Introduction to reactive intermediates. Free radicals: production, stability, conformations, solvent effects, abstraction, addition reactions, rearrangements. Radicals in synthesis: alkane halogenations, radical oxidations. Carbenes and nitrenes, preparation and their reactions, electronic structure, singlet vs. triplet.Arynes: generation, structure, reaction with nucleophiles, cycloadditions.Carbenes: generation, structures, triplet vs. singlet carbenes, reactions1,3-Dipoles: generation, structures, cycloaddition reactions, stereospecificity of reactions. Synthesis and reactions of phosphorous and sulfur ylides. Wittig reaction and modifications.2. Molecular re-arrangements: C to C migrations. Migratory aptitudes, anchimeric assistance and neighbouring group participation. Pinacol and related rearrangements3. Aromatic heterocyclic chemistry: pi-excessive and pi deficient rings, synthesis of heterocyclic compounds, (pyridine, pyrene, furan, thiophone, indole, quinoline, isoquinoline). Reactions of heterocycles with nucleophiles and electrophiles..

Asymmetric Synthesis.
Introduction: What is asymmetric synthesis? How to control selectivity?Part A: C-C bond formation.Nucleophilic addition to carbonyl compounds: Substrate control and Reagent control. Cram's model, Felkin-Anh model, Stereoselectivity of enolate formation. Alkylation of enolates. The aldol reaction. Chiral Auxiliaries. Asymmetric Aldol reaction. Nucleophilic addition to imine compounds. Mannich Reaction. Asymmetric Friedel Crafts.Part B: Asymmetric reduction. Organoboranes, hydrogenation (substrate control) Part C: Asymmetric addition to C=C. Hydroboration, Hydrosilyation, Epoxidation, Aziridination, Dihydroxylation, Hydroamination..

Assessment Breakdown
Continuous Assessment	0%	Examination Weight	100%

Course Work Breakdown
Type	Description	% of total	Assessment Date

Reassessment Requirement
Resit arrangements are explained by the following categories; 1 = A resit is available for all components of the module 2 = No resit is available for 100% continuous assessment module 3 = No resit is available for the continuous assessment component
This module is category 1

Indicative Reading List

Other Resources

None

Array

Programme or List of Programmes

BSc in Chemical and Pharmaceutical Sc.

BSSA

Study Abroad (DCU Business School)

BSSAO

Study Abroad (DCU Business School)

ECSA

Study Abroad (Engineering & Computing)