CHEM302 - Organic Chemistry
CHEM 302 Organic Chemistry is an 18-point paper available in the second semester.
It focuses on how the concepts and techniques of organic chemistry may be applied to interpret chemical reactions and to plan chemical transformations. The principles involved apply equally to reactions performed in the laboratory and to those proceeding in living systems. It is an essential course for chemistry majors wishing to proceed to a career that involves organic chemistry, and for all general degree students requiring knowledge and understanding of the organic chemistry to underpin their major subject. Chemical knowledge and practical experimental ability in organic chemistry to the level of CHEM 202 is recommended for entry into this course.
The topics covered in CHEM 302 are:
- Frontier molecular orbital theory and reactive intermediates
- Examination of the transformations involving carbocations, carbenes and free radicals, including reactions which involve structural rearrangements. Pericyclic reactions such as electrocyclic reactions, cycloadditions and 1,3-dipolar additions will also be studied. The emphasis will be to develop a toolkit of methods for the construction of the structural framework of organic molecules. An underlying theoretical basis will be the use of pictorial representations of molecular orbitals to interpret the selectivity of chemical reactions and to develop predictive tools for use in designing new chemical transformations.
- Heterocyclic Chemistry
- Structure, nomenclature, aromaticity and reactivity of heterocycles.
- Synthesis of heterocycles via condensation and pericyclic reactions.
- Cross-coupling reactions of heterocycles.
- Molecules of living systems
- Neighbouring group effects: bridged reaction intermediates, rate acceleration, rearrangements, organometallic catalysis, asymmetric induction.
There are three lectures and one four-hour laboratory class each week.
Lecture times and venues
Semester 2 Monday, Tuesday and Wednesday at 12.00 noon
Selected lecture material is available here.
Semester 2 Tuesday or Wednesday at 2.00 pm (Chemistry Labs, second floor, Science I)
The laboratory course will involve three sets of experiments over the course of 11 practical sessions.
Expectations at the completion of the course
- An understanding of the basic principles of molecular orbital theory as applied to pericyclic reactions and the reactions of some carbon-centred reactive intermediates, the structure and reactivities of simple heterocyclic aromatic compounds, the chemistry of simple carbenes, carbocations and free radicals and the concepts governing nucleophilic rearrangement reactions, the concepts of retrosynthetic analysis
- An ability to work efficiently and effectively in a multistep laboratory synthesis, while planning ahead to reduce any perceived hazards
- An ability to analyse critically an experimental procedure and write a formal report using standard scientific terminology
- An attainment of varying knowledge of pericyclic reactions, reactions of carboncentred reaction intermediates, the chemistry of heterocyclic aromatic compounds, synthetic reaction analysis, reagent choice, compound purification and spectroscopic characterization
Interdisciplinary perspective, self-motivation, lifelong learning, communication
Three-hour written examination 70%
Laboratory assessment 30%
Bruice, P.Y. Organic Chemistry, (4th edn), Prentice-Hall
March, J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure , (4th or 5th edn), Wiley
Prof David Larsen, Associate Professor James Crowley, Dr Eng Tan, Dr Bill Hawkins