CHY8422 : Pericyclic and radical reactions
- Offered for Year: 2022/23
- Module Leader(s): Dr Michael Hall
- Lecturer: Dr Julian Knight
- Owning School: Natural and Environmental Sciences
- Teaching Location: Newcastle City Campus
Semesters
| Semester 1 Credit Value: | 10 |
| ECTS Credits: | 5.0 |
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)
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
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
Teaching Methods
Teaching Activities
| Category | Activity | Number | Length | Student Hours | Comment |
|---|---|---|---|---|---|
| Structured Guided Learning | Lecture materials | 24 | 1:00 | 24:00 | Lectures |
| Guided Independent Study | Assessment preparation and completion | 22 | 0:30 | 11:00 | Revision for 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 | 61:00 | 61:00 | N/A |
| Total | 100:00 |
Jointly Taught With
| Code | Title |
|---|---|
| CHY8835 | Pericyclic and radical reactions |
Teaching Rationale And Relationship
In online lecture materials students learn advanced concepts in the organic chemistry of reactions involving cyclic transition states and radical intermediates which, encompasses synthetic, theoretical and mechanistic principles.
Assessment Methods
The format of resits will be determined by the Board of Examiners
Exams
| Description | Length | Semester | When Set | Percentage | Comment |
|---|---|---|---|---|---|
| PC Examination | 120 | 1 | A | 100 | Including computer based MCQ and long answers |
Exam Pairings
| Module Code | Module Title | Semester | Comment |
|---|---|---|---|
| CHY8835 | Further Organic Chemistry | 1 | N/A |
Assessment Rationale And Relationship
The alternate assessments 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 assessment 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.
Reading Lists
Timetable
- Timetable Website: www.ncl.ac.uk/timetable/
- CHY8422's Timetable