CH4112 Advanced Organic Transformations I
Aims:
a)
To understand the fundamentals of biological and organic photochemistry and to learn the use of photochemistry in organic synthesis, To illustrate the importance and synthetic utility of reactive intermediates, to learn how intermediates are generated and can be used to direct chemical reactions in a selective manner.
Outcomes:
On successful completion of this module the student should be able to:
- explain the basic biological photochemical processes
- analyze organic molecules for their photochemical reactivity
- plan industrially relevant syntheses used in photoreactors
- understand "green" concepts in synthesis
b)
To understand the fundamentals of radical chemistry and its application in organic synthetic chemistry. Their generation using radical initiators, stability and structure will be explored using carbon as well as hetero atom based radicals. The emphasis on the use of radical chemistry in modern organic synthesis to form structures that are both structurally simple as well as complex (such as natural products) using both inter- or intramolecular bond formation will be explored. Classical radical reactions such as the pinacol and the McMurrey reactions will be examined, as well as the generation of alkyl radicals using xanthates. The idea of cascade chemistry using radical (tandem or sequential) reactions will be introduced as well as the role of many radical initiators such as trialkyltin hydrides will be investigated using various examples from the literature.
Outcomes:
On successful completion of this module the student should be able to:
- Explain the structure, stability and reactivity of radicals
- Understand their formation using radical initiators, light or electro chemistry
- Draw out mechanism for radical reactions and explain their reactivity based on structure.
- Understand in general terms, and more specifically, radical reactivity (both carbon as well as heteroatom based), the radical-chain reaction, and the use of radicals in generating cis-fused ring systems, etc.
c)
Being able to explore their use in tandem inter- and intamolecular reactions.c)
To develop an in-depth understanding of the structure, reactivity and synthetic applications of both carbenes and nitrenes. To highlight the important synthetic utility of these reactive intermediates in modern organic synthesis. To learn how these intermediates can be applied towards the preparation of complex organic molecules, including a focus on recent literature examples and applications.
Outcomes:
On successful completion of this module the student should be able to
- Explain the structure, nomenclature and hydridisation of carbenes and nitrenes
- Understand the difference between singlet and triplet carbenes
- Know several methods for generating carbenes and nitrenes
- Discuss how these reactive intermediates can be employed in organic synthesis