NES8807 : Pericyclic and radical reactions
NES8807 : Pericyclic and radical reactions
- Offered for Year: 2024/25
- Module Leader(s): Dr Michael Hall
- Lecturer: Dr Matt Hopkinson, Dr Julian Knight
- Owning School: Natural and Environmental Sciences
- Teaching Location: Newcastle City Campus
Semesters
Your programme is made up of credits, the total differs on programme to programme.
| Semester 1 Credit Value: | 10 |
| ECTS Credits: | 5.0 |
| European Credit Transfer System | |
Pre-requisite
Modules you must have done previously to study this module
Pre Requisite Comment
Students require a minimum of a good understanding of organic chemistry at FHEQ Level 6
Co-Requisite
Modules you need to take at the same time
Co Requisite Comment
N/A
Aims
To introduce and develop the concepts of thermal and photochemical pericyclic reactions and Frontier Molecular Orbital (FMO) theory; to describe the methods used to determine the mechanisms of such reactions; to discuss radical chemistry; to explore reactions involving radicals and ions in cyclisation reactions.
Outline Of Syllabus
Pericyclic reactions and Frontier Molecular Orbital Theory (FMO)
Dr JG Knight
1-3 Molecular Orbitals and revision of the application of Frontier MO theory to ionic (and radical) processes
and relevance to Hard and Soft Acid and Base theory.
Construction of basic FMO's for linear conjugated pi-systems.
Introduction to pericyclic reactions.
4-6 Cycloaddition reactions. The Diels-Alder reaction: mechanism, Frontier-Orbital analysis, stereospecificity.
The effect of substituents on FMO energies and coefficients. Stereoselectivity and regioselectivity in
Diels-Alder reactions. Cheletropic reactions and 1,3-dipolar cycloadditions. Photochemical cycloaddition
reactions. The Woodward-Hoffmann rules.
7-8 Electrocyclic reactions.
9-11 Sigmatropic reactions. Group transfer reactions.
12 Revision lecture
Radical Reactions
Dr MJ Hall
1-2 Introduction to free radicals: generation of radicals (thermal, photochemical, electrochemical), properties
and reactivity, SOMO, hard vs. soft.
3-4 Stoichiometric radical processes: removal of functional groups and other applications in synthesis.
5-7 Kinetics of radical reactions: chain reactions, polymerisation, the use of tin centred radicals,
applications in synthesis, alternatives for tin.
8 Ring closing reactions: predicting ring closure with Baldwin’s rules and cascade processes.
9-11 Modern advances in radical chemistry
12 Revision lecture
Learning Outcomes
Intended Knowledge Outcomes
• understand Frontier Molecular Orbital (FMO) theory
• know the major types of pericyclic reactions
• understand the chemistry of radicals
• know how radicals are involved in cyclisation reactions
• know Baldwin’s rules
Intended Skill Outcomes
Subject specific or professional skills, able to:
• interpret experimental evidence and use this to elucidate reaction mechanisms
• apply FMO theory appropriately
• apply Baldwin’s rules to ring closure reactions
Cognitive or intellectual skills, able to:
• draw curly arrow mechanisms for a wide range of reactions that proceed via cyclic transition states
• solve problems of synthesis and mechanism with respect to such reactions
• analyse the kinetics of ring closure reactions
Key skills, able to:
• search the primary scientific literature to identify examples of relevance to the module
Teaching Methods
Teaching Activities
| Category | Activity | Number | Length | Student Hours | Comment |
|---|---|---|---|---|---|
| Structured Guided Learning | Lecture materials | 2 | 1:00 | 2:00 | Online via Canvas - Lecture material delivered online, non-synchronous |
| Structured Guided Learning | Lecture materials | 21 | 1:00 | 21:00 | Online via Canvas - Lecture material delivered online, non-synchronous |
| Guided Independent Study | Assessment preparation and completion | 24 | 0:50 | 20:00 | Revision for end of module assessment |
| Guided Independent Study | Assessment preparation and completion | 1 | 5:00 | 5:00 | MCQ assessment |
| Guided Independent Study | Assessment preparation and completion | 1 | 5:00 | 5:00 | Alternate assessment |
| Scheduled Learning And Teaching Activities | Drop-in/surgery | 4 | 1:00 | 4:00 | Online - 4 live meetings to be spread evenly through out semester 1 |
| Guided Independent Study | Independent study | 1 | 43:00 | 43:00 | Background reading |
| Total | 100:00 |
Teaching Rationale And Relationship
In online lectures students learn advanced concepts in the organic chemistry of reactions involving cyclic transition states and radical intermediates which, encompasses synthetic, theoretical and mechanistic principles.
Reading Lists
Assessment Methods
The format of resits will be determined by the Board of Examiners
Exams
| Description | Length | Semester | When Set | Percentage | Comment |
|---|---|---|---|---|---|
| Digital Examination | 120 | 1 | A | 100 | Including computer-based MCQ and long answers. |
Assessment Rationale And Relationship
The alternate assessment and multiple choice questions will test the students’ knowledge and understanding of the content of this module in the context of both synthetic and mechanistic chemistry.
Study Abroad students may request to take their exam before the semester 1 exam period, in which case the format of the paper may differ from that shown in the MOF. Study Abroad students should contact the school to discuss this.
Timetable
- Timetable Website: www.ncl.ac.uk/timetable/
- NES8807's Timetable
Past Exam Papers
- Exam Papers Online : www.ncl.ac.uk/exam.papers/
- NES8807's past Exam Papers
General Notes
Original Handbook text:
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The information contained within the Module Catalogue relates to the 2024 academic year.
In accordance with University Terms and Conditions, the University makes all reasonable efforts to deliver the modules as described.
Modules may be amended on an annual basis to take account of changing staff expertise, developments in the discipline, the requirements of external bodies and partners, and student feedback. Module information for the 2025/26 entry will be published here in early-April 2025. Queries about information in the Module Catalogue should in the first instance be addressed to your School Office.