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Module

CHY8422 : Pericyclic and radical reactions

  • Offered for Year: 2020/21
  • 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)
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

Teaching Methods

Please note that module leaders are reviewing the module teaching and assessment methods for Semester 2 modules, in light of the Covid-19 restrictions. There may also be a few further changes to Semester 1 modules. Final information will be available by the end of August 2020 in for Semester 1 modules and the end of October 2020 for Semester 2 modules.

Teaching Activities
Category Activity Number Length Student Hours Comment
Structured Guided LearningLecture materials221:0022:00Online via Canvas - Lecture material delivered online, non-synchronous
Structured Guided LearningLecture materials21:002:00Online via Canvas - Lecture material delivered online, non-synchronous
Guided Independent StudyAssessment preparation and completion17:007:00Online - alternative online assessment
Guided Independent StudyAssessment preparation and completion17:007:00Online - Multiple choice exam
Guided Independent StudyAssessment preparation and completion220:3011:00Revision for assessment
Scheduled Learning And Teaching ActivitiesDrop-in/surgery41:004:00Online - 4 live meetings to be spread evenly through out semester 1
Guided Independent StudyIndependent study147:0047:00N/A
Total100:00
Jointly Taught With
Code Title
CHY8835Further Organic Chemistry
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

Please note that module leaders are reviewing the module teaching and assessment methods for Semester 2 modules, in light of the Covid-19 restrictions. There may also be a few further changes to Semester 1 modules. Final information will be available by the end of August 2020 in for Semester 1 modules and the end of October 2020 for Semester 2 modules.

The format of resits will be determined by the Board of Examiners

Other Assessment
Description Semester When Set Percentage Comment
Written exercise1M50Alternate assessment for topics covered in first half of semester
Written exercise1M50Alternate assessment for topics covered in second half of semester
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