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The University of Southampton
Courses

CHEM2005 Aspects of Organic Synthesis

Module Overview

Aims and Objectives

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. 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.

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

Resources & Reading list

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

D T Davies. Aromatic Heterocyclic Chemistry. 

A. Randazzo. Guide to NMR Interpretation. 

J A Joule, K Mills. Heterocyclic Chemistry. 

S Warren. Organic Synthesis: The Disconnection Approach. 

P Sykes. Guidebook to mechanism in Organic Chemisty. 

Assessment

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.

Summative

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

Referral

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

Repeat Information

Repeat type: Internal & External

Linked modules

Pre-requisite: CHEM2001

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