CH3O2-Advanced Organic Chemistry - Contemporary Synthetic Methodology

Module Provider: Chemistry
Number of credits: 10 [5 ECTS credits]
Level:6
Terms in which taught: Spring term module
Pre-requisites: CH2OR1 Further Organic Chemistry
Non-modular pre-requisites:
Co-requisites:
Modules excluded:
Module version for: 2016/7

Module Convenor: Prof Laurence Harwood

Email: l.m.harwood@reading.ac.uk

Summary module description:
The course aims to relate advanced topics in organic chemistry to topics covered in previous modules and provide a foundation of knowledge to enable a better understanding of the primary chemical literature.

Aims:
The course aims to relate advanced topics in organic chemistry to subject areas covered in previous modules and provide a foundation of knowledge to enable a better understanding of the primary chemical literature.

Assessable learning outcomes:
Students who have successfully completed this module will be able to:
• Describe the use of a variety of metal-based reagents in organic synthesis.
• Construct relatively complex organic molecules revealing synthetic strategies for target synthesis.
• Describe the generation and reactivity of carbon centred radicals in organic synthesis.
• Be able to describe the rules governing pericyclic reactions and outline their use in organic synthesis.

Additional outcomes:
Through the provision of lectures and tutorials students will develop a broader appreciation of the expansive nature of modern synthetic organic chemistry. The ability of each student to understand and apply this knowledge will be developed via a number of small group tutorials.

Outline content:
A T Russell (6 lectures) Advanced Organometallic Chemistry
Principles and special features of reactions catalysed by transition metal complexes. The course will focus on cyclisation reactions and the Suzuki, Heck and Stille reactions.

L M Harwood (7 lectures) Orbital Symmetry
Electrocyclisations, sigmatropic rearrangements, cheletropic rearrangements and cycloadditions. Frontier molecular orbital rules for stereochemical and regiochemical prediction. Woodward-Hoffman rules and Huckel-Möbius interactions. Reactions covered will include [2+2], [3+2] and [4+2] cycloadditions including the Diels-Alder reaction, [3.3] sigmatropic rearrangements including the Claisen and Cope reactions and [1.3], [1.5], [1.7] hydride and alkyl shifts.

F J Davis (6 lectures) Heterocyclic Chemistry
Synthesis and reactions of pyrroles, furans, thiophenes, indoles, pyridines, quinolines and isoquinolines.

L M Harwood (7 lectures) Advanced Organic Synthesis and Retrosynthetic Analysis
Strategies involved in the construction of complex natural products. The central role of the carbonyl group in retrosynthetic analysis will be reviewed. The synthesis of a range of structurally complex molecules will be described.

Brief description of teaching and learning methods:
Two one hour lectures per week with approximately one tutorial on related material every two weeks.

Contact hours:
  Autumn Spring Summer
Lectures 26
Tutorials 3
Guided independent study 71
       
Total hours by term 100.00
       
Total hours for module 100.00

Summative Assessment Methods:
Method Percentage
Written exam 80
Set exercise 20

Other information on summative assessment:
Tutorial work and oral contribution at tutorials 20%
Students will attend 3 tutorials on the material covered in this module. Attendance is compulsory. A tutorial comprises both written work and oral contribution. A maximum of 20 marks is available for the written work and 5 marks for the oral contribution for each tutorial set.

Submission Dates:
Tutorials to be submitted as detailed on Blackboard

Formative assessment methods:

Penalties for late submission:

For students on chemistry-based degree courses any unexplained absence from more than two tutorials in chemistry in any term will automatically incur a formal warning from the School Director of Teaching and Learning.
The Module Convenor will apply the following penalties for work submitted late, in accordance with the University policy.
  • where the piece of work is submitted up to one calendar week after the original deadline (or any formally agreed extension to the deadline): 10% of the total marks available for the piece of work will be deducted from the mark for each working day (or part thereof) following the deadline up to a total of five working days;
  • where the piece of work is submitted more than five working days after the original deadline (or any formally agreed extension to the deadline): a mark of zero will be recorded.

  • The University policy statement on penalties for late submission can be found at: http://www.reading.ac.uk/web/FILES/qualitysupport/penaltiesforlatesubmission.pdf
    You are strongly advised to ensure that coursework is submitted by the relevant deadline. You should note that it is advisable to submit work in an unfinished state rather than to fail to submit any work.

    Length of examination:
    1.5 hours

    Requirements for a pass:
    An overall mark of 40%.

    Reassessment arrangements:
    Reassessment will be held in August and will be by examination only worth 100%.

    Final year students are not eligible to resit this module unless they have failed their degree programme overall.

    Additional Costs (specified where applicable):
    1) Required text books:
    2) Specialist equipment or materials:
    3) Specialist clothing, footwear or headgear:
    4) Printing and binding:
    5) Computers and devices with a particular specification:
    6) Travel, accommodation and subsistence:

    Last updated: 21 December 2016

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