Module: Organic Chemistry

Latest Module Specifications

Current Academic Year 2025 - 2026

Module Title	Organic Chemistry
Module Code	CHM1027 (ITS: CS307)
Faculty	Chemical Sciences	School	Science & Health
NFQ level	8	Credit Rating	5

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	24	No Description
Independent Study	101	No Description
Total Workload: 125

Section Breakdown
CRN	10258	Part of Term	Semester 1
Coursework	0%	Examination Weight	0%
Grade Scale	40PASS	Pass Both Elements	Y
Resit Category	RC1	Best Mark	N
Module Co-ordinator	Nessan Kerrigan	Module Teacher	Blanaid White, Mary Pryce, Patrick O'Malley

Type	Description	% of total	Assessment Date
Assessment Breakdown
Formal Examination	End-of-Semester Final Examination	100%	End-of-Semester

Reassessment Requirement Type
Resit arrangements are explained by the following categories; RC1: A resit is available for both^* components of the module. RC2: No resit is available for a 100% coursework module. RC3: No resit is available for the coursework component where there is a coursework and summative examination element. ^* ‘Both’ is used in the context of the module having a coursework/summative examination split; where the module is 100% coursework, there will also be a resit of the assessment

Pre-requisite	None
Co-requisite	None
Compatibles	None
Incompatibles	None

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 (5 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 (6 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.

Indicative Reading List

Books:

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,

Articles:
None

Other Resources

None