Year of entry: 2021

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Course unit details:

Core Chemistry 1
Unit code CHEM30411

Credit rating 10

Unit level Level 3

Teaching period(s) Semester 1

O ered by Department of Chemistry

Available as a free choice unit? No

Overview
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Stereoselective Synthesis (Dr Nathan Owston, 8 lectures)

1. Diastereoselectivity in ring systems: conformational analysis and stereoelectronics

2. Diastereoselectivity in acyclic systems

Prochirality

Reactions at C=O: Prochirality, Felkin-Anh model, Chelation control

Reactions at C=C: Houk model

Reactions of enolates: alkylation and aldol reactions, cyclic transition states

Diastereoselective reactions in synthesis: production of single enantiomers

3. Asymmetric synthesis

Chiral pool approaches

Chiral auxiliaries (alkylation/aldol reactions)

Chiral reagents

Resolution

4. Introduction to Asymmetric Catalysis

Catalysis with transition metals (asymmetric reduction of ketones)

Organocatalysis (asymmetric conjugate addition)

5. Applications of stereoselective reactions in synthesis ( ne chemicals, pharmaceuticals)

Reactive Intermediates (Dr Roger Whitehead, 8 lectures)

1.Introduction

Neutral reactive intermediates

Carbenes, Nitrenes, Arynes              

2. Radicals

What are radicals?

The structure of carbon-centred radicals

The relative stability of di erent radical species

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Historical aspects of radical chemistry

Sources of radical intermediates

Radical reactions in synthesis

Solving unseen problems involving radical intermediates

Pericyclic Reactions (Dr Daniele Leonori, 8 lectures)

1. Introduction

Covalent bonding

Frontier molecular orbitals (FMOs)

2. The Diels-Alder [4¿ + 2¿] cycloaddition reaction

FMO interactionsStereoselectivity and regioselectivity

Substituents e ects

3. Other cycloaddition reactions

[2 + 2] Processes ('forbidden' and 'allowed' variants)

Other (4n + 2) and 4n pairings

4. Selection rules and orbital symmetry

Cycloadditions exempli ed

5. Electrocyclic reactions
Introduction to electrocyclic reactions

Conservation of orbital symmetry in the ring-opening of cyclobutene

Hexatriene–cyclohexadiene

6. Sigmatropic rearrangements

[1,5] and [1,7] Hydrogen shifts

[1,3] Sigmatropic shifts

[3,3] Sigmatropic rearrangements

Cope and Claisen rearrangements

 
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Pre/co-requisites
Unit title Unit code Requirement type Description

Structure and reactivity of organic molecules CHEM20412 Pre-Requisite Compulsory

Organic Synthesis CHEM20411 Pre-Requisite Compulsory

Aims
The unit aims to develop further understanding of synthetic and mechanistic organic chemistry
with emphasis on reactive intermediates and elements of stereochemistry.
 

Learning outcomes
On successful completion of the course students should be able to:

Apply knowledge of molecular structure, reactivity and stereochemistry to both rationalise

and predict the      stereochemical outcome of chemical reactions

Evaluate and propose strategies for the synthesis of complex molecules which include
stereoselective reactions.

Describe the various types of reactive intermediates that are of importance in organic
chemistry and explain the physical properties and chemical reactivity of such species;

Describe the factors that in uence the structure, stability and reactivity of di erent radical
species and explain the outcome of important reaction processes;

Describe the various reaction types undergone by synthetically useful free radicals;

Predict and rationalise the outcome of unseen transformations involving reactive

intermediates;

Understand the fundamental of molecular orbital analysis in pericyclic reactions;

Be able to rationalise the stereochemical outcome of pericyclic reactions;

Teaching and learning methods

 
 

Transferable skills and personal qualities

Enhance transferable skills in the areas of problem solving and analysis
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Assessment methods
Method Weight

Written exam 100%

Feedback methods
Example classes and individual feedback from tutors/lecturers
 

Recommended reading
• C.J.Moody and G.H.Whitham, Reactive Intermediates (An Oxford Chemistry Primer) ISBN: 978-0-
198-55672-5

• A.F.Parsons, An Introduction to Free Radical Chemistry (Wiley-Blackwell, 2000) ISBN: 978-0-632-

05292-9

• J. Clayden, N. Greeves, S. Warren and P. Wothers, Organic Chemistry (Oxford University Press,
2001) ISBN 0198503466  (Chapters 35 and 36).

• J. Clayden, N. Greeves and S. Warren, Organic Chemistry 2nd edition (Oxford University Press,
2012) ISBN 0199270295
(http://ukcatalogue.oup.com/product/9780199270293.do#.UYTABOCTGSh)  (Chapters 34 and 35).

• I. Fleming, Pericyclic Reactions (Oxford Chemistry Primer, 2nd Edition) (Oxford University Press,
2015)  ISBN 0199680900 (https://global.oup.com/academic/product/pericyclic-reactions-
9780199680900?q=9780199680900&lang=en&cc=gb) (a ordable, thorough guidebook).

• I. Fleming, Molecular Orbitals and Organic Chemical Reactions: Student Edition (Wiley-
Blackwell, 2009)  ISBN 0470746599 (http://eu.wiley.com/WileyCDA/WileyTitle/productCd-
0470746599.html) (a comprehensive reference text).

• G. Procter,  Stereoselectivity in Organic Synthesis (Oxford Chemistry Primers) (Oxford

University Press, 1998) ISBN 978-0198559573.

• Access to a set of Orbit molecular models is essential.

 

Study hours
Scheduled activity hours

Assessment written exam 2

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Scheduled activity hours

Lectures 21

Practical classes & workshops 3

Independent study hours

Independent study 74

Teaching sta
Sta member Role

Daniele Leonori Unit coordinator

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