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The University of Southampton

CHEM2005 Aspects of Organic Synthesis

Module Overview

Aims and Objectives

Module Aims

The aim of this course is to provide a core for future studies in chemistry and allied subjects, in aspects of Organic Chemistry as specified below and a continuation in the development of basic practical skills including safe working practices (risk, hazard and control measures), laboratory report writing (written and verbal communication of results), error and accuracy. Teaching in this course is substantially synoptic, and extensively uses lecture material from the core organic courses in year 1 and the first semester of year 2. Lecture component: The aim of this organic chemistry course is to provide an introduction of retrosynthetic analysis and the disconnection approach. These are fundamental concepts used by organic chemists in designing the synthesis of target molecules in sectors such as pharmaceuticals, agrochemicals and fine chemicals. In the second part of the course, students are exposed to the basic principles and concepts of heterocyclic chemistry, with an emphasis on the synthesis and reactivity of heteroaromatic compounds and of applying retrosynthetic analysis principles. Practical component: The aim of the practical component of the module is to provide students with the skills that will be needed in their future practical work. Instruction is provided regarding the in the presentation of practical reports, awareness of health and safety procedures, practical skills in the laboratory (and the theory on which they are based) and problem solving in the practical situation. This course builds on the skills learned in the previous year and term. Students will undertake as series of three experiments, of which the titles below are examples: • Biginelli Project (multicomponent reactions) • Carbocycles (aldol and Michael chemistry) • Pyrazole heterocycle (heterocyclic chemistry) Each experiment is also preceded by a prelaboratory exercise that involves a combination of audio visual resources, accessible via Blackboard that will help prepare you for the experimental work. A short quiz based on this content is to be completed before starting practical work. There are separate learning outcomes for each experiment and these are further specified in the practical scripts. Finally, there is one workshop at the beginning of the course, dedicated to the interpretation of NMR spectra. There is a pre-workshop presentation which revises key principles. The workshop itself is focused on the determination of coupling constants, and its application on structural determination which is a main application of NMR in organic chemistry labs.

Learning Outcomes

Learning Outcomes

Having successfully completed this module you will be able to:

  • the ability to demonstrate knowledge and understanding of essential facts, concepts, principles and theories relating to retrosynthetic analysis and heterocyclic chemistry
  • the ability to apply such knowledge and understanding to the solution of problems related to the synthesis of organic target molecules
  • skills in communicating synthetic organic chemistry
  • Evaluate the risks associated with an experiment and understand how to mitigate against those risks.
  • Set up glassware and apparatus to conduct experiments in Organic Chemistry.
  • Interpret data from a range of physical techniques to characterise Organic compounds.
  • Present the results of a practical investigation in a concise manner.


1) Retrosynthetic Analysis and the Disconnection Approach • Introduction to retrosynthetic analysis and the disconnection approach. • Functional Group Interconversions. Application to the synthesis of amines (amide reduction, reductive amination, nitrile, nitroalkane alkylation/reduction • Timing of disconnections: synthesis of aromatic compounds (regioselectivity), reactions of aromatic side chains (emphasis on reversal of directing effects) • Protecting groups (Benzyl ether, THP ether, silyl ether, acetal, phthalimide, carbamate) • Functional Group Additions. Ester and ketone alkylation, malonate and acetoacetate chemistry. Decarboxylations. • 1,3-disconnections. Aldol, Reformatski, (Horner-) Wittig, Knoevenagel, Mannich, Claisen, conjugate addition • 1,5-disconnections: enolate conjugate addition • 1,4-disconnections: Umpolung. Reactions of thioketals as an acyl anion synthon, nitro compounds • 1,2-disconnections. Epoxide opening, pinacol and acyloin couplings, alkene dihydroxylation • Alkene formation. Wittig reactions, alkyne reductions (synthetic applications of acetylenes) • Ring formation methods. Dieckmann condensation, Birch reduction of aromatic rings, Robinson annelation, pinacol and acyloin couplings, Diels-Alder (brief). 2) Synthetic Manipulation of Specific Functional Groups • Application of important methodology (aldol reactions, conjugate addition, electrophilic aromatic substitution, heterocycle synthesis) • Application of spectroscopic methods in organic characterisation. Coupling constants in cyclohexane chair conformations, C-F and H-F couplings. 3) Aromaticity and the Chemistry of Aromatic Hetrocycles • Structure and bonding in benzene and COT, Hückel rules, aromatic ions and introduction to aromatic heterocycles. • Overview of the importance of aromatic heterocycles in biochemistry, technology, medicine and agriculture. • Principles of reactivity and ring-synthesis of aromatic heterocycles. • Pyrrole, furan and thiophene: structure, reactivity and synthesis. • Pyrazolones and azlactones: structure, reactivity and synthesis • Indole and benzofuran: structure, reactivity and synthesis. • Imidazole, oxazole and thiazole: structure, reactivity and synthesis. • Pyridine, pyridinium, quinoline and isoquinoline: structure, reactivity and synthesis. 4) NMR analysis: -Understanding multiplicity -Ability to measure coupling constants -Interpretation of coupling constant values in a structural context

Learning and Teaching

Teaching and learning methods

Lectures, tutorials, problem class, workshop, practicals Practical hours includes pre-laboratory e-learning. Preparation for scheduled sessions hours includes other independent study.

Completion of assessment task24
Preparation for scheduled sessions57
Practical classes and workshops29
Total study time150

Resources & Reading list

A. Randazzo. Guide to NMR Interpretation. 

S Warren. Organic Synthesis: The Disconnection Approach. 

D T Davies. Aromatic Heterocyclic Chemistry. 

J Clayden, N Greeves and S Warren. Organic Chemistry. 

J A Joule, K Mills. Heterocyclic Chemistry. 

P Sykes. Guidebook to mechanism in Organic Chemisty. 


Assessment Strategy

All absences from practical sessions must be validated and unexcused absences will result in failure of the module. Repeat year externally: allowed if practical attendance criteria has been met. The practical marks are retained, the theory assessment is exam only. Repeat year internally: note that practical may be reassessed by resubmission of reports or repeated.


MethodPercentage contribution
Assessed Tutorials 10%
Examination  (2 hours) 65%
Lab proficiency %
Practical write-ups 25%


MethodPercentage contribution
Examination  (2 hours) 100%
Lab proficiency %

Repeat Information

Repeat type: Internal & External

Linked modules

Pre-requisite: CHEM2001

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