C 22J SPECTROSCOPY, CARBANIONS AND AROMATIC SYSTEMS (4 Credits) (Semester I)

Pre-requisites:
C 10J and C 10K
Syllabus:
Spectroscopy - The application of spectroscopic techniques in organic chemistry: electronic, infra-red and proton magnetic resonance spectroscopy and their utility in elucidating the structure of organic molecules.
Carbanions - Carbanions as intermediates in carbon-carbon bond formation. The alkylation and acylation of carbanions. Aldol and related reactions. Cyclisation reactions.
Aromatic systems - Carbocyclic and heterocyclic compounds. The concept of aromaticity. Electrophilic and nucleophilic substitution in benzenoid systems. Polycyclic aromatic compounds - naphthalene, anthracene and phenanthrene. The synthesis and reactions of five- and six-membered heterocycles. Fused ring systems - indole, benzofuran, quinoline and isoquinoline.
A practical course of 36 hours.

C32J SYNTHESIS, MECHANISM STEREOCHEMISTRY IN ORGANIC CHEMISTRY (4 Credits). (Semester II)

Pre-requisites:
C 10J and C10K
Co-requisite:
C 22J
Syllabus:
Methods and reagents in organic synthesis. Methods of effective reduction, oxidation, formation of carbon-carbon single and double bonds, cyclisation actions. Mechanistic Interpretations.
General mechanistic features of the main types of organic reactions - substitution, addition, elemination, cyclisation - including the intermediacy of carbocations and free radicals.
Stereochemistry of organic molecules. Static and dynamic aspects.
The synthesis and properties of amino acids and carbohydrates.
A practical course of 36 hours.

C 32K THE CHEMISTRY OF ORGANIC NATURAL PRODUCTS (4 Credits) (Semester I)

Pre-requisite:
C 22J
Syllabus:
General Biosynthesis. Determination of metabolic pathways. Mechanism of enzyme reactions; coenzymes and cofactors; overview of primary metabolism; isotopic labelling and incorporation methods.
Aspects of classification, reactions, synthesis and biosynthesis: Monosaccharides and their derivatives; oligosaccharides. Alkaloids, penicillins, cephalosporins. Polyketides, macrolides, prostaglandins and leucotrienes. Iso prenoids; Steroids.
The functions and uses of natural products.
A practical course of 36 hours.

C 32L ORGANIC SYNTHESIS: STRATEGY AND CONTROL (4 Credits) (Semester I)

Pre-requisites:
C 22J and C 32J
Syllabus:
The synthesis of selected biologically active and structurally interesting compounds.
The design of organic syntheses. The Disconnection Approach. Carbon-carbon bond formation reactions. Functional Group Modification. Synthetic strategy - Retrosynthetic Analysis.
Methods of achieving chemoselectivity. Stereoselective and stereospecific reactions. Chiral synthesis.
A practical course of 36 hours.

C 32M MECHANISTIC ORGANIC CHEMISTRY AND PHOTOCHEMISTRY (4 Credits) (Semester II)

Pre-requisites:
C 22J and C 32J
Syllabus:
Mechanistic interpretation of organic reactions. Carboxylic esters and acids - Hydrolysis, decarboxylation. Elimination reactions. Symmetry controlled reactions; Frontier Molecular Orbital approach, Simple correlation diagrams and aromatic transition state theory applied to electrocylic, cyloaddition and sigmatropic rearrangement reactions. Nucleophilic substitution reactions; nucleophilicity; carbocations; leaving group effects; neighbouring group participation.
Linear free energy relationships. Kinetic vs thermodynamic control of reactions. Kinetic isotope effects. Hard and soft acids and bases.
Photochemistry of carbonyl groups. Photochemistry of alkenes and dienes. Reactions involving singlet oxygen.
Aspects of radical chemistry.
A practical course of 36 hours.

C 32N ORGANIC CHEMISTRY IN MEDICINE AND AGRICULTURE (4 Credits) (Semester II)

Pre-requisites:
C 22J and C 32J
Syllabus:
The synthesis of organic compounds of medicinal and agricultural interest. General principles of drug action; Structure-Activity Relationships; Principles of drug design. Synthetic approaches to selected pharmacologically active compounds e.g. sulphonamides, pyrimidines, penicillins, central nervous system drugs - tranquillizers, antidepressants, hallucinogens. Insecticides, fungicides, herbicides, growth regulators.
Natural products used in medicine and agriculture.
A practical course of 36 hours.


Return to Chemistry, UWI-Mona, Home Page
May-95,rjl