This module builds on the student’s knowledge of carbonyl chemistry, aromatic chemistry and stereochemistry. The module objectives are to give a detailed understanding of advanced organic chemistry in terms of transformation, mechanism and application in the synthesis of biological and medicinal targets.
Learners will explain the synthetic utility of the α-carbon in terms of ring formations, with an emphasis on the synthesis of biologically active compounds. The synthesis and reactivity of heterocyclic organic compounds will be examined, with an emphasis on the chemistry of biologically active heteroatom-containing compounds. Students will also outline the relationship between structure and reactivity, with a particular focus on substituent effects.
In addition, this module builds on the student’s knowledge of structural elucidation principles and extends this to the application of more complex spectroscopic methods by means of problem-solving workshops.
Advanced carbonyl chemistry with a focus on ring formation (intramolecular Aldol, Dieckmann, Robinson Annulation).
Rearrangements with a focus on mechanism and application in the synthesis of biologically active compounds.
- Pinacol/semipinacol rearrangement
- Dienone-phenol rearrangement
- Benzilic acid rearrangement
- Favorskii rearrangement
- Baeyer Villeger reaction
- Beckmann rearrangement
Physical Organic Chemistry – relating structure and reactivity with a focus on either Hammett equation (σ and ρ values) or solvent effects and isotope effects.
Heterocyclic Chemistry with a focus on synthetic strategy and use of protecting groups for the preparation of biologically active or important heterocycles.
- Cyclization Reactions – nucleophilic addition and intramolecular nucleophilic displacement
- Cycloaddition reactions
Reactivity and uses of Heterocyclic Compounds
Aromatic Five-Membered-Ring Heterocycles
- Pyrrole, furan and thiophene
- Indole, benzofuran, and benzothiophene
Aromatic Six-Membered-Ring Heterocycles
- Quinoline and isoquinoline
- Purine and pyrimidine
Other Biologically Important Heterocycles and Natural Products
- Heterocyclic vitamins
Spectroscopic Structure Elucidation of Organic Compounds
Delivered through problem-solving workshops. Learners will use NMR to analyse mixtures, be introduced and use 2D NMR spectra, analyse the coupling in NMR spectra and correlate the coupling constant with structure. The workshops will also include analysis and interpretation of the following spectroscopic data:
- UV-Vis and IR spectroscopic data (review)
- Mass Spectra
- 1H NMR Spectroscopy
- 13C NMR Spectroscopy
- Advanced practical classes with a focus on structural elucidation using spectroscopic techniques.
Students will learn through lectures (20 hours), problem solving (4 hours), workshops (8 hours) and self directed learning (68 hours).
|Module Content & Assessment