Module: Organic Chemistry

Module Specifications..

Current Academic Year 2023 - 2024

Please note that this information is subject to change.

Module Title	Organic Chemistry
Module Code	CS307
School	School of Chemical Sciences
Module Co-ordinator	Semester 1: Nessan Kerrigan Semester 2: Nessan Kerrigan Autumn: Nessan Kerrigan
Module Teachers	Pat O'Malley Blanaid White Emma Coyle Hasim Ibrahim Nessan Kerrigan
NFQ level	8	Credit Rating	5
Pre-requisite	None
Co-requisite	None
Compatibles	None
Incompatibles	None

Repeat the module

Description

This modules discusses physical chemistry in the context of organic reactions – what determines reactivity of intermediates, how can reaction outcomes be predicted? This provides insight into mechanisms of reactions, for example those of reactive intermediates (radicals, 1,3-dipoles, carbenes, arynes, ylides). Frontier molecular orbital theory is also introduced. Also considered is selectivity of reactions, in particular in the context of three-dimensional chemistry. The concepts of reagent and substrate controlled stereochemistry in asymmetric synthesis are outlined.

Learning Outcomes

1. Identify well-known reactive intermediates and their reactions
2. Explain the reactivity of intermediates, based on thermodynamic and kinetic principles
3. Predict the products and selectivity of reaction pathways
4. Design regio- and stereoselective syntheses

*Type*	*Hours*	*Description*
Workload	Full-time hours per semester
Lecture	30	No Description
Independent Study	95	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

Physical organic chemistry (1 week)
Review of fundamental principles of chemical thermodynamics and kinetics. Transition state theory. Reaction rate expressions. General relationships between thermodynamic stability and reaction rates. Kinetic versus thermodynamic control. Curtin-Hammett principle. Kinetic isotope effects. Linear free-energy relationships.

Reactive intermediates (4 weeks)
Introduction to reactive intermediates. Radicals: production, stability, conformations, solvent effects, abstraction, addition reactions, rearrangements. Carbenes and nitrenes, preparation and their reactions, electronic structure, singlet vs. triplet. Arynes: generation, structure, reaction with nucleophiles, cycloadditions. Synthesis and reactions of phosphorous and sulfur ylides. Wittig reaction and modifications.1,3-Dipoles: generation, structures, cycloaddition reactions, stereospecificity of reactions, frontier molecular orbital (FMO) theory.

Asymmetric synthesis (5 weeks)
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%

Type	Description	% of total	Assessment Date
Course Work Breakdown

Reassessment Requirement Type
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

J. Clayden, S. Warren, N. Greeves: 2012, Organic Chemistry, 2nd, Oxford University Press, Oxford,
F. Carey, R. Sundberg: 2007, Advanced organic chemistry: Part A Structure and mechanisms, 5th, 3, Springer, New York,
G. Zweifel, M. Nantz: 2007, Modern Organic Synthesis, 1st, W. H. Freeman,

Other Resources

None

Programme or List of Programmes

AC	BSc in Chemical and Pharmaceutical Sc.
BSSA	Study Abroad (DCU Business School)
BSSAO	Study Abroad (DCU Business School)
HMSA	Study Abroad (Humanities & Soc Science)
HMSAO	Study Abroad (Humanities & Soc Science)
IESA	Study Abroad (Institute of Education)
IESAO	Study Abroad (Institute of Education)
SHSA	Study Abroad (Science & Health)
SHSAO	Study Abroad (Science & Health)
SMPSC	Single Module Prof. Science and Health

Date of Last Revision

17-JUN-08

Archives: