Organic Synthesis


Unit code: CHEM20411
Credit Rating: 10
Unit level: Level 2
Teaching period(s): Semester 1
Offered by School of Chemistry
Available as a free choice unit?: N

Requisites

Prerequisite

Aims

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

     
  • The chemistry of the carbonyl group: exploitation of stabilised carbanions in organic synthesis;
  •  
  • Structural relationship in Organic Chemistry;
  •  
  • Introduction to Heterocyclic Chemistry.

Overview

Weeks 1-4 Chemistry of the Carbonyl Group (Dr Peter Quayle, 7 lectures & 1 workshop)

  • carbonyl group: reactivity
  • keto-enol tautomerism: spectroscopic studies
  • deprotonation and pKa's 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; synthesis of small organic molecules


Weeks 5-8: Structural Relationship in Organic Chemistry (Professor Mike Greaney, 7 lectures & 1 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

Weeks 9-12: Introduction to Heterocyclic Chemistry (Dr Nathan Owston, 7 lectures & 1 workshop)

  • 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

 

 

Teaching and learning methods

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

Learning outcomes

  • 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

Transferable skills and personal qualities

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

Assessment methods

  • Written exam - 100%

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

Copies of presentation material used will be supplied and be available via Blackboard

Feedback methods

  • Assessed tutorial work: written feedback
  • Model answers to tutorial questions will be posted on Blackboard at the end of each unit.
  • Feedback on examination performance via tutors

Study hours

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

Teaching staff

Peter Quayle - Unit coordinator

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