65202 Organic Chemistry 1
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Credit points: 6 cp
Result type: Grade and marks
Requisite(s): 65212 Chemistry 2 OR 65213 Chemistry 2 (Advanced)
Description
This subject introduces the reactions characteristic of the common families of carbon compounds and explores the details and implications of the reaction mechanisms involved. A primary objective is for students to gain an appreciation of the relationship of molecular structure to reactivity across a broad range of functional groups.
Students have the opportunity to perform many of these reactions in the laboratory, and to evaluate the success of their experiments by analysis of their reaction products using infra-red spectroscopy as well as melting point, boiling point and refractive index measurements. These are skills required for professional chemists.
Subject learning objectives (SLOs)
Upon successful completion of this subject students should be able to:
| 1. | Apply fundamental concepts in chemical structure and bonding, including functional groups, to the rationalization of reactions of organic molecules |
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| 2. | Apply the concepts of electron pushing to the fundamental organic reaction mechanisms |
| 3. | Apply logical thinking to evaluate, analyse and use information from different sources |
| 4. | Analyse and solve problems in organic chemistry |
| 5. | Conduct experiments, analyse data, summarize results and report them in an appropriate scientific format |
| 6. | Work as an effective member of a team and manage workload required for scientifically based practice and professional work |
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)
Contribution to the development of graduate attributes
1. Disciplinary knowledge
An understanding of nature, practice, and application of organic chemistry are learned through asynchronous online material and enhanced through problem-solving workshops. In the practical classes, students explore a range of organic chemical reactions and their applications through weekly hands-on experiments. Students are assessed on the mastering of the subject via the application, explanation, and analysis of accumulative knowledge in the quizzes, lab reports, and core competency assessment exercise.
2. Research, Inquiry and Critical Thinking
Scientific curiosity and problem-based learning are learned through laboratory programs and workshops that are designed to provoke inquiry and conceptual thinking. Students are encouraged to discuss experimental observations, analysis of results and problems with each other and their lab supervisor in practical classes.
In the laboratory, students will develop the ability 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
Critical to scientific practice is the development of logical thought and problem-solving skills in experimental work. These skills are learned via working responsibly and safely while carrying out the synthesis of organic compounds.
Data handling and synthesis will be developed through the practical program. Ongoing laboratory data collection and preparation occurs every week in the practical. Data presentation is assessed in reports.
Teamwork, ethics and professional conduct is learned as students work in groups in practical classes. Students learn to delegate, share tasks and work collaboratively in order to achieve the aims of the experiment.
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.
Teaching and learning strategies
The subject will be delivered through hands-on practical sessions, problem-based workshops, and asynchronous online material. Students access resources via Canvas and can complete workshop questions before classes. Active learning, including hands-on practicums, in-class discussions, and team-based experiments, will be incorporated into the sessions. Students participate in problem-solving exercises and class discussions. Students are asked to study key content and solve questions before coming to the workshop sessions. The workshop session time will be used to actively engage students in further exploring concepts in a collaborative learning environment. During the in-class time, students will collaboratively provide and discuss their answers in which the feedback will be given during class.
In the laboratory, students will work collaboratively in groups of 2-3 throughout the sessions. Students will explore a range of organic chemical reactions and their applications through weekly hands-on practical classes. Students will engage in collaborative learning by working in small groups to conduct experiments and collect data. They will also develop their time management and teamwork skills. Students will learn to communicate their experimental results through the writing of a scientific report. While the students work in small groups in the prac classes, their assessment is individually based and their final interpretation and report write-up is a solo effort.
Students will receive verbal and written feedback on their submitted 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.
An aim of this subject is to develop academic and professional language and communication skills to succeed at university and in the workplace. During the course of this subject, you will complete a milestone assessment task that will, in addition to assessing your subject-specific learning objectives, assess your English language proficiency.
Content (topics)
1. Laboratory Techniques
Overview of organic chemistry laboratory techniques; melting point, recrystallization and chromatographic techniques. IR and 1H NMR spectroscopy.
2. Review of first princliples, tools and skills
Structure and bonding, polar covalent bonds, acids and bases, arrow notation.
3. Stereochemistry
Optical rotation and asymmetry. Properties of Enantiomers, meso forms, racemates, diastereoisomers. Methods for resolution of a racemic mixture. Chiral molecules with chirality centres at atoms other than carbon.
4. Alkanes
Energies of C-C bond rotation in alkanes. Stabilities, energy and ring strain in cycloalkanes. Cis/trans isomerism in substituted cycloalkanes. Interconversion of cyclohexane chair forms. Free radical halogenation and its mechanisms and energy profiles.
5. Alkenes and Alkyne
Chemical reactions of alkenes. Mechanism of electrophilic addition to symmetrical and unsymmetrical alkenes. Radical addition of HBr. Radical and cationically initiated polymerisation. Preparation of alkenes from alkynes, and from alcohols and haloalkanes (Saytzeff rule). Kinetic and thermodynamic control of 1,2- and 1,4- additions to 1,3 dienes. Preparation of acetylene and higher alkynes. Reactions of alkynes.
6. Organic halogen compounds
Preparation from alcohols and from alkenes. Nucleophilic substitution reactions. SN1 and SN2 mechanisms, and their kinetics and stereochemistry. E1 and E2 elimination reactions. Factors influencing SN reaction rates and competition between substitutions and eliminations. Preparation and reactions of organometallic compounds.
7. Alcohols, phenols and ethers
Preparation of alcohols from haloalkanes, esters, alkenes, carbonyl compounds, and Grignard reagents. Reaction to form alkoxides, halides, esters, ethers and alkenes. Reactions of phenols to form phenoxides, esters, ethers. Contrast with alcohol reactions. Preparation of symmetrical ethers by dehydration of alcohols. Williamson ether synthesis (alkoxides with halogen compounds) for unsymmetrical ethers. Physical properties and chemical reactions.
8. Aldehydes and ketones
Nucleophilic addition reactions with water, alcohols, amines, cyanide ion and Grignard reagents; reduction with hydride reagents. Condensation to form imines. Oxidation. Haloform reaction.
9. Carboxylic acids and their derivatives
Conversion to acid chlorides, anhydrides, esters, amides, and nitriles. Relative reactivity of acid derivatives with water, alcohols, phenols and amines. Preparation of acids from alcohols or aldehydes by oxidation, from halo compounds, using Grignard or nitrile synthesis. Reduction of carboxylic acids and esters to alcohols, and of amides and nitriles to amines.
10. Amines
Relative basicities of aliphatic amines and anilines. Preparation from halogen and nitro compounds. Reactions with acids and haloalkanes. Reaction with carboxylic acid derivatives to give amides.
11. Aromatic Compounds
Resonance. Aromaticity and the Huckel 4n+2 rule. Electrophilic substitutions: nitration, sulfonation, halogenation, Friedel-Crafts alkylation, and acylation. Electrophilic substitution mechanism.
Assessment
Assessment task 1: Practical Work
| 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
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| Objective(s): | This assessment task addresses subject learning objective(s): 1, 2, 3, 5 and 6 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: | 45% |
| Criteria: | Students will be assessed on:
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Assessment task 2: Quizzes
| Intent: | This assessment task contributes to the development of the following graduate attributes: 1. Disciplinary knowledge 2. Research, Inquiry and Critical Thinking 5. Communication. |
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| Objective(s): | This assessment task addresses subject learning objective(s): 1, 2, 3 and 4 This assessment task contributes to the development of course intended learning outcome(s): 1.1, 2.1 and 5.1 |
| Type: | Quiz/test |
| 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 |
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| Objective(s): | This assessment task addresses subject learning objective(s): 1, 2, 3 and 4 This assessment task contributes to the development of course intended learning outcome(s): 1.1 and 2.1 |
| Type: | Laboratory/practical |
| Groupwork: | Individual |
| Weight: | 30% |
| Criteria: |
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Minimum requirements
English language proficiency: It is a requirement of this subject that you complete Assessment task 1 (the report, proformas and refection). Should you receive an unsatisfactory English language level, you may be required to complete further language support after the completion of this subject.
References
•D.E. Levy " Arrow Pushing in Organic Chemistry", Wiley, 2008.
•L.D.Field, S. Sternhell and J.R. Kalman “Organic Structures from Spectra”, 5th ed, Wiley