65508 Organic Chemistry 2
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Credit points: 6 cp
Result type: Grade and marks
Requisite(s): 65202 Organic Chemistry 1
Description
This subject builds on previous studies of functional group reactions and spectroscopic techniques and illustrates applications of these concepts for organic synthesis. Topics covered include aromaticity and chemistry of benzene and heterocyclic compounds; carbanion chemistry and multi-step synthesis of new aromatic compounds; chemistry of phenols and aryl halides; palladium-catalysed coupling reactions and modern synthetic methods used in academia and industry; pericyclic reactions and 1,3-dipolar [2+3] cycloadditions. The subject emphasises the practical applications of organic chemistry in the synthesis of many important compounds. Chemical research literacy in organic chemistry is implemented, using SciFinder Scholar, with an emphasis on differentiating and using chemical literature.
In the laboratory, students have the opportunity to perform multi-step reactions to synthesise bioactive molecules as well as carrying out other useful synthetic transformations.
Subject learning objectives (SLOs)
Upon successful completion of this subject students should be able to:
| 1. | Apply of key concepts in chemical structure and bonding, including functional groups, to the rationalization of reactions of organic molecules |
|---|---|
| 2. | Apply fundamental organic reaction mechanisms |
| 3. | Synthesise organic compounds in the laboratory using modern synthetic methods and strategies |
| 4. | Critically evaluate, analyse and summarise information from a range of scholarly sources |
| 5. | Apply analytical and problem-solving skills to investigate organic chemical synthesis |
| 6. | Analyse and interpret experimental results, and communicate them in a formal scientific format |
Course intended learning outcomes (CILOs)
This subject also contributes specifically to the development of following course intended learning outcomes:
- Demonstrate theoretical and technical knowledge of organic, inorganic, analytical, and physical chemistry and be able to explain specialised knowledge in one or more sub-disciplines. (1.1)
- Evaluate scientific evidence and apply effective experimental design, analysis and critical thinking to test current chemistry knowledge. (2.1)
- Work autonomously or in teams to address workplace or community problems utilising best scientific practice, and to act safely and responsibly in chemistry laboratory and practical settings. (3.1)
- Effectively communicate concepts and scientific discovery in chemistry using different formats to present information in professional or public settings. (5.1)
- Recognise Aboriginal and Torres Strait Islander people’s unique connection to country and ways of knowing to inform professional capability to work inclusively and ethically with and for Indigenous Australians in Chemistry contexts. (6.1)
Contribution to the development of graduate attributes
This subject is intended to develop the following graduate attributes:
1. Disciplinary knowledge
An understanding of the nature, practice and application of organic chemistry are learned through asynchronous online material and enhanced through practical classes and problem-solving tutorials. Students are assessed on the mastering of the subject via the application, explanation, and analysis of accumulative knowledge in the tutorial quizzes, lab reports, and core competency assessment exercise.
2. Research, Inquiry and Critical Thinking
Critical thinking and problem-based learning are learned through laboratory programs and tutorials, which are designed to provoke inquiry and conceptual thinking. Students are encouraged to discuss reaction mechanisms, experimental observations, analysis of results and problems with each other and their lab supervisor in practical classes.
In the laboratory, students get hands-on experience preparing and conducting experiments to synthesise organic compounds of scientific interest. Students will develop the ability to prepare experimental methods using a flowchart to address how a synthetic pathway can be practically and safely achieved. Students will learn to acquire and interpret scientific data and make reasonable judgments beyond the current experiments to broader scientific principles. Students have the opportunity to use relevant scientific evidence plus literature to assess and evaluate their experimental outcomes. These will be assessed through the laboratory reports.
3. Professional, Ethical and Social Responsibility
Professional and ethical scientific practice is developed via working responsibly and safely in the laboratory while carrying out the synthesis of organic compounds. This process is assessed via report marking criteria.
Literature search skills are developed using SciFinder to gather and evaluate information from sources such as research and review articles published in the scientific literature. Students apply these skills in their lab reports and are also assessed as part of the criteria for lab reports.
Data handling and synthesis will be developed through the practical program. Ongoing laboratory data collection and preparation of write-up, in the laboratory notebook, occur every week in the practical. Data presentation is assessed via report marking criteria.
Prioritisation of time devoted to learning is developed through strictly time-limited in practical classes. Through the practical program, students learn to develop time management skills through the need to prioritise the reaction steps in their experimental program to maximise the efficient use of their time. Targeted learning is guided by the experimental schedule in the lab manual. This is indirectly assessed via the ability of students to complete the experiment and submit the report on time.
Ethics and professional conduct in science are learned through lectures and report feedback. This includes a full discussion of the reasons against and consequences of data fabrication and plagiarism. Plagiarism software is used to monitor submitted work.
5. Communication
Excellence in written scientific communication is developed through the process of writing scientific reports. These skills are developed through the practical classes and are aimed at the effective communication in written work and in the use of chemical structures, report discussion, and conclusion. Clear and logical writing that follows standard practice in scientific communication is assessed.
Spoken communication is developed by preparing and delivering an oral presentation of a laboratory report. Students will be assessed on clarity explanation, logical flow and presentation of their answers.
6. Aboriginal and Torres Strait Islander Knowledges and Connection with Country
Modern chemistry often involves interacting with many cultural perspectives and knowledge systems. Knowledge of Indigenous Australian contexts to inform professional cultural capabilities to work effectively with and for Indigenous Australians within scientific contexts will be developed through written work exploring these aspects from a chemistry perspective.
Teaching and learning strategies
The subject will be delivered through eleven weeks of workshops and ten weeks of hands-on practical sessions. Active learning, including hands-on practicums and in-class discussions will be incorporated into workshops and practical sessions. During workshops, students participate in problem-solving exercises and the class discussions. Students can work collaboratively to solve problems. During the in-class time, students are asked to provide and discuss their answers, in which the feedback will be given during class.
In the practical sessions, students will explore a range of organic chemical reactions and their applications through weekly hands-on practical classes. Students will conduct experiments and collect data. Through these practical sessions, they will also develop their time management skills. Students will learn to communicate their experimental results through the writing of a laboratory book. Their assessment is individually based, and final interpretation and report write-up is a solo effort.
Students will receive verbal and written feedback on their work. Students are also encouraged to discuss with peer and tutors to make the most of the lab time. Written feedback on each report will be given to the student within two weeks of submission. The student will provide the opportunity to reflect on feedback by writing a one-page reflection to how it can be used to improve their scientific report writing.
Content (topics)
1. Aromatic Chemistry
Structure and nomenclature of aromatic compounds. Electrophilic substitution and effects of substituents. Transformation of substituents. Designing synthetic sequences for poly-substituted benzene compounds, using retrosynthetic analysis. Review of important syntheses of aromatic compounds including selectivity.
2. Heterocyclic Compounds
An introduction to the chemistry of aromatic heterocyclic compounds. Structure and reactivity of 5-membered ring system (pyrrole, furan and thiophene), 6-membered ring system (pyridine) and fused-ring heterocycles (quinoline, isoquinoline and indole).
3. Chemical Research Literacy
Chemical literature searching will be explored, with aim to allow students to learn how to find, assess, retrieve, interpret and evaluate information in the chemical literature (online and offline). SciFinder Scholar will be used for (i) subject searching and (ii) structure searching.
4. Carbanion Reactions
Carbonyl a-substitution reactions and chemistry of enolate ions. Carbonyl condensation reactions in terms of aldol, Claisen condensation and related reactions such as Knoevenagel, Dieckmann cyclization and Perkin condensation. Carbonyl nucleophilic alkyl substitutions, e.g. in acetoacetic ester and malonic ester syntheses. Nucleophilic addition of α,β-unsaturated carbonyl compounds (e.g. Michael reaction, Stork Reaction and Robinson annulation). Synthesis of alkenes from aldehydes and ketones, using Wittig reaction.
5. Pd-catalyzed C–C bond forming reactions
Homogenous Pd-catalyzed reactions will be described in term of Heck reactions, Stille reactions, Suzuki cross-coupling reactions, Sonogashira reactions. The applications of these reactions for the synthesis of organic compounds will be discussed. Microwave assisted Pd-catalyzed reactions will also be discussed.
6. Pericyclic Reactions
Pericyclic reactions in terms of cycloaddition reactions which include Diels-Alder reactions will also be described together with their mechanisms using frontier molecular orbital theory. 1,3-Dipolar [2+3] cycloaddition reactions and their applications in the “Click” chemistry.
In addition the laboratory work includes:
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Preparation of a local anesthetic, Lignocaine
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Synthesis of tetrahydroisoquinoline
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Synthesis of a bioactive compound, Flavonol
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A Wittig reaction: Preparation of 1,4-diphenyl-1,3-butadiene
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Pd-catalyzed Suzuki coupling reaction
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The Diels-Alder Reaction
Assessment
Assessment task 1: Laboratory Reports
| Intent: | This assessment task contributes to the development of the following graduate attributes: 1. Disciplinary knowledge 2. Research, Inquiry and Critical Thinking 3. Professional, Ethical and Social Responsibility 5. Communication 6. Aboriginal and Torres Strait Islander Knowledges and Connection with Country |
|---|---|
| Objective(s): | This assessment task addresses subject learning objective(s): 1, 2, 3, 4 and 6 This assessment task contributes to the development of course intended learning outcome(s): 1.1, 2.1, 3.1, 5.1 and 6.1 |
| Type: | Laboratory/practical |
| Groupwork: | Individual |
| Weight: | 45% |
| Criteria: | Students will be assessed on:
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Assessment task 2: Tutorials
| Intent: | This assessment task contributes to the development of the following graduate attributes: 1. Disciplinary knowledge 2. Research, Inquiry and Critical Thinking 3. Professional, Ethical and Social Responsibility 5. Communication |
|---|---|
| Objective(s): | This assessment task addresses subject learning objective(s): 1, 2, 4 and 5 This assessment task contributes to the development of course intended learning outcome(s): 1.1, 2.1, 3.1 and 5.1 |
| Type: | Exercises |
| Groupwork: | Individual |
| Weight: | 25% |
| Criteria: | Students will be assessed on:
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Assessment task 3: Core competency assessment
| Intent: | This assessment task contributes to the development of the following graduate attributes: 1. Disciplinary knowledge 2. Research, Inquiry and Critical Thinking 3. Professional, Ethical and Social Responsibility 5. Communication |
|---|---|
| Objective(s): | This assessment task addresses subject learning objective(s): 1, 2, 4 and 5 This assessment task contributes to the development of course intended learning outcome(s): 1.1, 2.1, 3.1 and 5.1 |
| Type: | Laboratory/practical |
| Groupwork: | Individual |
| Weight: | 30% |
| Criteria: | Students will be assessed on:
|
Minimum requirements
Practical classes in subjects offered by the Faculty of Science are an important and integral part of your learning in this subject. In addition to assisting students’ understanding of application of concepts, practical classes develop hands-on laboratory skills and experience, including safety skills and specialised techniques related to the assessment tasks. These also contribute to the development of essential graduate attributes desired by employers. Thus, students are strongly encouraged to attend all scheduled practical sessions.
If you cannot attend a scheduled practical class, please contact your subject coordinator as soon as possible to discuss your situation.
Recommended texts
- J McMurry, Organic Chemistry, 7th or 8th ed, Thomson, Brooks/ Cole, 2007 (ISBN 0495112585)
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David Klein, Organic Chemistry, 3rd ed, Wiley, ISBN: 9781119316152, ISBN: 9781119316152 [E-book]
- J Clayden, N Greeves, S Warren and P Wothers, Organic Chemistry, 2000, Oxford University Press (ISBN: 9780198503460).
- D E Levy, Arrow-Pushing in Organic Chemistry, An Easy Approach to Understanding Reaction Mechanism, John Wiley & Sons, 2008.
- J.A. Joule and K. Mills, Heterocyclic Chemistry, 4th ed, Blackwell, 2006 (ISBN-10:0-632-05453-0)
References
- P Y Bruice, Organic Chemistry, 4th ed, Pearson Education, 2004 (ISBN 0-13-121730-5)
- T W G Solomons, C B Fryhle, Organic Chemistry, 9th ed, John Wiley 2006 (ISBN 978-0-471-68496-1)
- D.L. Pavia, G.M. Lampman, G.S. Kirz, and J.R. Vyvyan, Introduction to Spectroscopy, 4th ed, Brooks/Cole, 2008.
- S N Ege, Organic Chemistry, 4th ed, Houghton, 1999 (ISBN 0-395-90223-1)
- M B Smith, J March, Advanced Organic Chemistry, 6th ed, John Wiley, 2007 (ISBN 978-0-471-72091-1)