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:
Non-modular pre-requisites:
Co-requisites:
Modules excluded:
Current from: 2020/1

Module Convenor: Dr Chris Smith

Email: c.d.smith@reading.ac.uk

Type of module:

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 o rganic 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.Ìý

Outline content:

Advanced Organometallic Chemistry (12 lectures): 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.

Orbital Symmetry (7 lectures): Electrocyclisations, sigmatropic rearrangements, cheletropic rearrangements and cycloadditions. Frontier molecular orbital rules for stereochemical and regiochemical prediction. Woodward-Hoffman rules and Huckel-Möbi us 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.

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

Advanced Organic Synthesis and Retrosynthetic Analysis (7 lectures): S trategies 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.Ìý

Contact hours:

Ìý	Autumn	Spring	Summer
Lectures		26
Seminars		3
Guided independent study:		71
Ìý	Ìý	Ìý	Ìý
Total hours by term	0		0
Ìý	Ìý	Ìý	Ìý
Total hours for module	100

Summative Assessment Methods:

Method	Percentage
Written exam	80
Set exercise	20

Summative assessment- Examinations:
1.5 hours

Summative assessment- Coursework and in-class tests:

On-line tests to be completed on Black Board based on material covered. Submission Dates: Test to be completed as detailed on Blackboard.

Formative assessment methods:

Tutorial work and oral contribution. Students will attend 3 seminars on the material covered in this module. Attendance is compulsory. A seminar comprises both written work and oral contribution. Submission Dates: Tutorials to be submitted as detailed on Blackboard.

Penalties for late submission:

The Module Convenor will apply the following penalties for work submitted late:

• where the piece of work is submitted after the original deadline (or any formally agreed extension to the deadline): 10% of the total marks available for that piece of work will be deducted from the mark for each working day[1] (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:
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.

Assessment 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):

Last updated: 4 April 2020