MChem Chemistry with International Study / Course details

Year of entry: 2023

Course unit details:
Organic Synthesis

Course unit fact file
Unit code CHEM20411
Credit rating 10
Unit level Level 2
Teaching period(s) Semester 1
Available as a free choice unit? No

Overview

This unit will comprise of three blocks of lectures which have been selected in order to exemplify how basic concepts relating to structure and bonding can be applied to chemical reactivity. Each block will consist of seven lectures together with an associated problems class. The problems classes will illustrate how the basic processes discussed in the lecture material can be applied to unseen problems; students will be encouraged to devise solutions to these problems in collaboration with their peers. This unit also serves to underscore the synoptic nature of organic chemistry.

The topics covered in this unit include:

i. The exploitation of stabilised carbanions in organic synthesis and an introduction to retrosynthetic analysis (Dr. Giacomo Crisenza)

ii. An introduction to Heterocyclic Chemistry (Prof. Simon Webb)
iii. Structural relationships in Organic Chemistry (Prof. Michael Greaney).

Pre/co-requisites

Unit title Unit code Requirement type Description
Structure and Reactivity CHEM10412 Pre-Requisite Compulsory

Aims

This unit will build upon the introduction to the chemistry of carbon compounds developed in CHEM10412. As core organic chemistry, the course unit wishes to provide a wide understanding of the occurrence, synthesis and behaviour of organic compounds.

    Learning outcomes

    On successful completion of the course students should be able to: 
      •  Apply models to describe the electronic structure/bonding in carbonyl-containing and  heteroaromatic compounds
    •    Predict the reactivity of carbonyl-containing compounds based on knowledge of structure and bonding 
    •    Apply spectroscopic techniques to the prediction of constitution of carbonyl compounds
    •    Propose methods for the synthesis of heteroaromatics from carbonyl precursors
    •    Describe and predict the observed reactivity of heteroaromatics based on knowledge of structure and bonding
    •    Propose and evaluate strategies for the synthesis of small molecules containing common functional groups and heteroaromatic structures
    •    Predict/rationalise stereochemical outcome of fundamental organic transformations 
    •    Apply stereoelectronic arguments to chemical reactivity

    Syllabus

    Weeks 1-4: Chemistry of the Carbonyl Group (Dr Giacomo Crisenza, 4 asynchronous lectures and 3 synchronous sessions)
    • carbonyl group: reactivity 
    • keto-enol tautomerism: spectroscopic studies
    • deprotonation and pKa values of simple carbonyl compounds and 1,3 dicarbonyl compounds; structural, stereoelectronic and solvent effects
    • reactions of enolate anions with electrophiles • enolate akylation, aldol condensations
    • Introduction to retrosynthetic analysis; common disconnections for C-X and C-C bonds; common functional group interconversions (FGIs) application to the synthesis of representative organic molecules.

    Weeks 5-8: Introduction to Heterocyclic Chemistry (Dr Simon Webb, 4 asynchronous lectures and 3 synchronous sessions)
    • biologically important heterocyclic compounds – natural products and drugs
    • electrophilic aromatic substitution/nucleophilic aromatic substitution
    • pyridine and pyrrole – properties and reactivity • furan and thiophene – properties and reactivity
    • indole, quinoline and isoquinoline • introduction to saturated heterocycles

    Weeks 9-12: Structural Relationship in Organic Chemistry (Professor Mike Greaney, 4 asynchronous lectures, 3 synchronous sessions & 1 potential workshop)
    • Cyclohexane chair and boat conformations, axial and equatorial bonds 
    • Diastereoisomers, meso compounds, threo and erythro nomenclature
    • Compounds with stereogenic centres
    • Restricted rotation and axial chirality; allenes and biaryls
    • Separation (resolution) of enantiomers
    • Assessment of enantiomeric purity
    • Prochirality, enantiotopicity and diastereotopicity • Stereoselective reactions

    Teaching and learning methods

    • Lectures
    • Workshops
    • Small-group tutorials
    • Online support using Blackboard.

    Transferable skills and personal qualities

    • Problem-solving skills
    • Communication skills
    • Numeracy and Mathematical skills
    • Analytical skills
    • Time management and organisational skills

    Assessment methods

    Method Weight
    Written exam 100%

    Feedback methods

    • Assessed tutorial work: written feedback. Feedback from tutors during tutorials
    • Model answers to tutorial questions will be posted on BlackBoard at the end of each unit
    • Mock paper (with outline solutions) to be posted on BlackBoard
    • Feedback during examples class and lectures
    • Feedback on examination performance via tutors

    Recommended reading

    J Clayden, N Greeves, S Warren and P Wothers, Organic Chemistry (Oxford University Press, 2nd Edition 2012), ISBN 978-0-19-927029-3. Main Library, blue area, floor 3.547.02 CLA.

    Available online: https://www.dawsonera.com/abstract/9780191666216

    Study hours

    Scheduled activity hours
    Assessment written exam 2
    Lectures 21
    Practical classes & workshops 3
    Tutorials 3
    Independent study hours
    Independent study 71

    Teaching staff

    Staff member Role
    Simon Webb Unit coordinator

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