The University of Southampton
Courses

CHEM2019 Intermediate Organic Chemistry II

Module Overview

The aim of this module is to provide a basis for future studies in chemistry and allied subjects. Students select two areas of Chemistry from Inorganic, Organic, and Physical Chemistry according to the needs of their programme of study. Please consult with the leader of your programme or your personal academic tutor in deciding which two modules to follow.

Aims and Objectives

Module Aims

The aim of this organic chemistry course is to provide an in-depth overview 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

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

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 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 functionalisation • 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. • • 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 and tutorials with group working and tutor support. Hours for Preparation for scheduled sessions includes other independent study.

TypeHours
Revision10
Preparation for scheduled sessions35
Tutorial6
Lecture24
Total study time75

Resources & Reading list

J A Joule, K Mills. Heterocyclic Chemistry. 

P Sykes. Guidebook to mechanism in Organic Chemisty. 

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

D T Davies. Aromatic Heterocyclic Chemistry. 

S Warren. Organic Synthesis: The Disconnection Approach. 

Assessment

Formative

In-class Test

Summative

MethodPercentage contribution
Examination  (2 hours) 100%

Referral

MethodPercentage contribution
Examination  (2 hours) 100%
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