The University of Southampton
Courses

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.

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.

Syllabus

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.

Learning and Teaching

Teaching and learning methods

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

TypeHours
Lecture24
Tutorial6
Completion of assessment task24
Revision10
Practical classes and workshops29
Preparation for scheduled sessions57
Total study time150

Resources & Reading list

D T Davies. Aromatic Heterocyclic Chemistry. 

P Sykes. Guidebook to mechanism in Organic Chemisty. 

J A Joule, K Mills. Heterocyclic Chemistry. 

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

S Warren. Organic Synthesis: The Disconnection Approach. 

Assessment

Assessment Strategy

If this module is core to the student’s programme a minimum mark of 40% must be obtained for the practical and examination components separately in addition to achieving the 40% module pass mark. If the module is taken as an option (compulsory) or an elective module a minimum mark of 25% must be obtained for the practical and examination components separately.

Summative

MethodPercentage contribution
Examination  (2 hours) 75%
Practical write-ups 25%

Referral

MethodPercentage contribution
Examination  (2 hours) 75%
Practical write-ups 25%
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