CVB301 Organic Chemistry: Strategies for Synthesis
To view more information for this unit, select Unit Outline from the list below. Please note the teaching period for which the Unit Outline is relevant.
| Unit code: | CVB301 |
|---|---|
| Prerequisite(s): | (CVB101 and CVB102 and CVB204) or (CVB204 and admission to ST20) |
| Equivalent(s): | PQB531 |
| Credit points: | 12 |
| Timetable | Details in HiQ, if available |
| Availabilities |
|
| CSP student contribution | $1,118 |
| Domestic tuition unit fee | $4,680 |
| International unit fee | $5,760 |
Unit Outline: Semester 1 2024, Gardens Point, Internal
| Unit code: | CVB301 |
|---|---|
| Credit points: | 12 |
| Pre-requisite: | (CVB101 and CVB102 and CVB204) or (CVB204 and admission to ST20) |
| Equivalent: | PQB531 |
| Coordinator: | Steven Bottle | s.bottle@qut.edu.au |
Overview
Learn skills in the synthesis of organic molecules and an analysis of the nature of the reaction mixtures and products generated. Apply the principles of synthetic design, using their knowledge of a range of synthetically useful organic reactions and the concept of retrosynthesis. You will learn to evaluate experimental data qualitatively and quantitatively, especially with regard to IR and NMR spectroscopic data, and use this knowledge to deduce and explain conclusions based on logical arguments. You will be able to use creative design strategies to overcome common synthetic organic problems by applying the principles of protecting group strategies and selectivity in organic synthesis.
The application of practical skills in safe laboratory practice relating to the principles of synthesis, isolation and purification of organic compounds will allow you to demonstrate their capabilities as well as develop skills to document their findings in an appropriate work orientated format.
Learning Outcomes
On successful completion of this unit you will be able to:
- Analysis of the synthesis of organic molecules by applying the principles of synthesis design, using the concepts of retrosynthesis and then proposing a synthetic pathway using your knowledge of a range of synthetically useful organic reactions.
- Evaluation of experimental data qualitatively and quantitatively, especially with regard to IR and NMR spectroscopic data, and use of this knowledge to deduce and explain conclusions based on logical argument
- Creative design strategies that can be used to overcome common synthetic organic problems by applying the principles of selectivity in organic synthesis
- Application of practical skills in safe laboratory practice relating to the synthesis, isolation and purification of organic compounds and document these findings in an appropriate work orientated format.
Content
Material covered will include but is not limited to
- Introduction to modern concepts in organic synthesis
- Discussion of heterocyclic and heteroaromatic chemistry
- Forward and retrosynthetic analysis of reaction mechanisms, with particular focus on carbon-carbon bond forming reactions, enolate chemistry, metal catalysed coupling reactions, and protecting groups strategies
- The synthesis and applications of biomolecules.
Learning Approaches
Class contact in this unit will involve a combination of traditional lectures and less formal interactive lecture/tutorials, and a sequential laboratory experiment.
Lectures/tutorials (26 hours, 2 hours per week)
One hour of lecture time is devoted to advice on the preparation of reports on practical work.
Practical work (24 hours, 6 x 4 hour sessions)
This consists of one large experiment - a multi-step synthesis involving a protecting group. Staff of the QUT Library will present a workshop on information retrieval in organic chemistry during the first practical session.
Workshops (10 hours, 5 x 2 hours)
These interactive sessions will allow a deeper exploration or revision of selected topics from the lecture program or the techniques used in the practical exercise. One will specifically cover NMR spectroscopy in more detail, to support the depth of understanding needed in the practical component of this unit.
Feedback on Learning and Assessment
Formative feedback will be provided during the semester.
Assessment
Overview
The assessment in this unit comprises both formative and summative elements. Formative assessment will take the form of provision of model answers for summative tasks, practice problems with worked solutions, regular feedback on your practical workbook, and interactive discussions with your laboratory demonstrators. Summative assessment is a combination of problem-solving tasks, final submission of the laboratory workbook, and a supervised written theory examination.
Unit Grading Scheme
7- point scale
Assessment Tasks
Assessment: Problem Solving Task
This assignment is comprised of a series of individualised problems involving the proposal of synthetic routes to target molecules from nominated starting materials and the proposal of a synthetic scheme starting from an individually assigned nominated starting substance.
This is an assignment for the purposes of an extension.
Assessment: Workbook
You will be required to undertake 3 4-hour sessions of supervised practical work for which you will maintain a laboratory workbook which documents the reaction being performed (including description of the mechanism), description of the synthetic procedure and workup (including flow diagram showing how the workup procedure is used to isolate and purify organic compounds), and an analysis of the spectroscopic data used to characterise your compounds. All of these results and analysis of spectral data supplied will be summarised in a final laboratory report
This is an assignment for the purposes of an extension.
Assessment: Theory Exam
The end of semester theory exam will cover content from theory components of the unit. You will be expected to solve problems on reaction mechanisms, stereochemistry, carbohydrate chemistry and biosynthesis. The retrosynthetic analysis will not be assessed in this exam.
Academic Integrity
Students are expected to engage in learning and assessment at QUT with honesty, transparency and fairness. Maintaining academic integrity means upholding these principles and demonstrating valuable professional capabilities based on ethical foundations.
Failure to maintain academic integrity can take many forms. It includes cheating in examinations, plagiarism, self-plagiarism, collusion, and submitting an assessment item completed by another person (e.g. contract cheating). It can also include providing your assessment to another entity, such as to a person or website.
You are encouraged to make use of QUT’s learning support services, resources and tools to assure the academic integrity of your assessment. This includes the use of text matching software that may be available to assist with self-assessing your academic integrity as part of the assessment submission process.
Further details of QUT’s approach to academic integrity are outlined in the Academic integrity policy and the Student Code of Conduct. Breaching QUT’s Academic integrity policy is regarded as student misconduct and can lead to the imposition of penalties ranging from a grade reduction to exclusion from QUT.
Resources
Molecular Models may be purchased in a package with the textbook by Bruice.
Resource books containing useful information and tutorial exercises will be provided, together with details of recommended websites.
Resource Materials
Recommended text(s)
Bruice PY (2007) Organic Chemistry, 5th edition, Pearson Education
Zubrick TW (2009) The Organic Chem Lab Survival Manual, 8th Edition, John Wiley & Sons
Risk Assessment Statement
The professional practice of Chemistry requires the safe handling of Hazardous Substances. A practical laboratory program is an important part of this unit, so you will be required to handle such substances. The chemicals and procedures used in this unit are deemed to be appropriate for students at this level of the course. You will undertake compulsory formal pre-laboratory assessment in Health and Safety matters relevant to the laboratory and QUT buildings in general. Health and Safety information and precautions relevant to the particular experiments are clearly explained in the Practical Manual. Having been provided with this advice, it is your responsibility to comply with all instructions, for the safety of yourself, your fellow students and staff.