CHEM 3620 - Organic Chemistry III

North Terrace Campus - Semester 1 - 2021

Organic chemistry provides the capabilities to replicate some of nature's most intriguing molecules and develop strategies and technologies to construct compounds that widely influence society. As part of the study of organic chemistry, we ask: how do we elucidate the structure of a molecule? Can we prove a reaction mechanism? How can we explain unusual organic chemical reactions? Can we use our mechanistic understanding to design efficient syntheses of complex organic molecules? This course firstly showcases the application of powerful physical methods, including nuclear magnetic resonance and mass spectrometry, to the structural analysis of organic molecules. Other tools of physical organic chemistry are then introduced to explain how fundamental reaction mechanisms are elucidated. The student's knowledge of simple reaction mechanisms is then extended to help rationalise more complex, multi-step transformations involving unstable intermediates such as carbocations, carbenes and radicals. Finally, this course shows how principles of organic reactivity can be used to design logical syntheses of complex organic compounds using retrosynthetic analysis.

  • General Course Information
    Course Details
    Course Code CHEM 3620
    Course Organic Chemistry III
    Coordinating Unit School of Physical Sciences
    Term Semester 1
    Level Undergraduate
    Location/s North Terrace Campus
    Units 3
    Contact up to 9 hours per week
    Available for Study Abroad and Exchange Y
    Prerequisites CHEM 2545 or equivalent; high-achieving students without pre-requisite may be granted exemption on application to Head of Chemistry
    Incompatible CHEM 3111
    Course Description Organic chemistry provides the capabilities to replicate some of nature's most intriguing molecules and develop strategies and technologies to construct compounds that widely influence society. As part of the study of organic chemistry, we ask: how do we elucidate the structure of a molecule? Can we prove a reaction mechanism? How can we explain unusual organic chemical reactions? Can we use our mechanistic understanding to design efficient syntheses of complex organic molecules? This course firstly showcases the application of powerful physical methods, including nuclear magnetic resonance and mass spectrometry, to the structural analysis of organic molecules. Other tools of physical organic chemistry are then introduced to explain how fundamental reaction mechanisms are elucidated. The student's knowledge of simple reaction mechanisms is then extended to help rationalise more complex, multi-step transformations involving unstable intermediates such as carbocations, carbenes and radicals. Finally, this course shows how principles of organic reactivity can be used to design logical syntheses of complex organic compounds using retrosynthetic analysis.
    Course Staff

    Course Coordinator: Associate Professor David Huang

    Course Timetable

    The full timetable of all activities for this course can be accessed from Course Planner.

  • Learning Outcomes
    Course Learning Outcomes
    On successful completion of this course, students will be able to:
    1 understand fundamental principles of spectroscopic methods and apply methodology to interpret spectra for unknown samples in order to determine their structure.
    2 understand the mechanisms of organic reactions, and apply these transformations to the design and synthesis of complex molecules.
    3 apply the principles of retrosynthetic analysis to the design of efficient syntheses of organic molecules and understand issues of selectivity (including chemo-, regio-, and steroselectivity) as applied to complex molecule synthesis.
    4 demonstrate proficiency in undertaking individual and/or team-based laboratory investigations using appropriate apparatus and safe laboratory practices, including the collection, analysis, interpretation and communication of results of an experiment.
    5 design and plan an investigation by selecting and applying appropriate practical and/or theoretical techniques or tools.
    University Graduate Attributes

    This course will provide students with an opportunity to develop the Graduate Attribute(s) specified below:

    University Graduate Attribute Course Learning Outcome(s)
    Deep discipline knowledge
    • informed and infused by cutting edge research, scaffolded throughout their program of studies
    • acquired from personal interaction with research active educators, from year 1
    • accredited or validated against national or international standards (for relevant programs)
    1-5
    Critical thinking and problem solving
    • steeped in research methods and rigor
    • based on empirical evidence and the scientific approach to knowledge development
    • demonstrated through appropriate and relevant assessment
    1-5
    Teamwork and communication skills
    • developed from, with, and via the SGDE
    • honed through assessment and practice throughout the program of studies
    • encouraged and valued in all aspects of learning
    4
    Career and leadership readiness
    • technology savvy
    • professional and, where relevant, fully accredited
    • forward thinking and well informed
    • tested and validated by work based experiences
    1-5
    Intercultural and ethical competency
    • adept at operating in other cultures
    • comfortable with different nationalities and social contexts
    • able to determine and contribute to desirable social outcomes
    • demonstrated by study abroad or with an understanding of indigenous knowledges
    4,5
    Self-awareness and emotional intelligence
    • a capacity for self-reflection and a willingness to engage in self-appraisal
    • open to objective and constructive feedback from supervisors and peers
    • able to negotiate difficult social situations, defuse conflict and engage positively in purposeful debate
    4,5
  • Learning Resources
    Required Resources
    There is no prescribed text for this course. All required course material will be provided by the course instructor(s).
    Recommended Resources
    Textbooks
    • Clayden, Greeves, and Warren, Organic Chemistry (Oxford University Press)
    • Silverstein, Webster, Kiemle, and Bryce, Spectroscopic Identification of Organic Compounds (Wiley)
    All of these texts are available for loan from the Barr Smith library. References to other material and recent literature will be given in lectures.
    Online Learning
    Teaching materials and course documentation will be posted on the MyUni website (http://myuni.adelaide.edu.au/).
  • Learning & Teaching Activities
    Learning & Teaching Modes
    This course consists of the following components:
    • Lectures/Tutorials: 12 x 3 hours per week (timetabled as "Workshops")
    • Practicals: 8 x 5.5-hour sessions with one session per week
    • Workshop: 3 x 5.5-hours sessions run during a Practical timeslot
    Workload

    The information below is provided as a guide to assist students in engaging appropriately with the course requirements.

    A student enrolled in a 3 unit course, such as this, should expect to spend, on average 12 hours per week on the studies required. This includes both the formal contact time required to the course (e.g., lectures and practicals), as well as non-contact time (e.g., reading and revision).
    Learning Activities Summary
    Coursework
    Course material will cover the following topics:
    • Spectroscopy & Structure Determination (8 lectures)
    • Physical Organic Chemistry (4 lectures)
    • Advanced Organic Reactions (6 lectures)
    • Strategies and Tactics of Synthesis (6 lectures)
    Spectroscopy workshop
    The spectroscopy workshop will reinforce concepts in molecular structure determination. Students will work in small groups under the guidance of a senior academic to interpret real examples of spectroscopic data and identify unknown chemical compounds using spectroscopic techniques.

    Practicals
    Practical exercises will provide students with "hands on" experience in the design and conduct of contemporary organic chemistry experiments. These skills-based sessions will allow students to develop their control of chemical reactivity, synthesise and isolate molecular targets, and characterise the structure and properties, all in a safe manner. Training and direction on communicating the results of these investigations in various formats will be provided.

    Tutorials
    Tutorial sessions will be held weekly and will provide the student with the opportunity to discuss material from the lecture course. Formative tutorial questions will be used to reinforce the concepts introduced in lectures through a combination of qualitative and quantitative problem solving.
    Specific Course Requirements
    Attendance is compulsory at all scheduled chemistry practical sessions. The learning outcomes for this course are substantially dependent on laboratory experience and practice. Therefore, missing any practical class or failing to submit a reasonable attempt at any practical report in a semester will result in a grade of FAIL being recorded for the course. Students with medical or compassionate reasons for non-attendance will be given an opportunity to make up missed practical sessions.
  • Assessment

    The University's policy on Assessment for Coursework Programs is based on the following four principles:

    1. Assessment must encourage and reinforce learning.
    2. Assessment must enable robust and fair judgements about student performance.
    3. Assessment practices must be fair and equitable to students and give them the opportunity to demonstrate what they have learned.
    4. Assessment must maintain academic standards.

    Assessment Summary
    Assessment Task Task Type Weighting Hurdle
    yes/no
    Learning Outcome Due
    Summative Assignments Formative & Summative 10% No 1,2,3 Weeks 9-12
    Workshop Assignment Formative & Summative 10% No 1,4,5 Week 6
    Practical Reports Formative & Summative 30% No 1,2,4

    Weeks 5-12

    Examination Summative 50% Yes
    (45%)
    1-3 Exam period
    Assessment Related Requirements
    Assessment Item % needed to meet course requirement Additional Assessment
    Examination 45% Yes - RAA Exam;
    a grade of at least 45% must obtained
    Practical work is compulsory Satisfactory completion of all practicals, including attendance of ALL practical sessions and reasonable attempt at ALL practical reports Missed practicals can be made up
    Assessment Detail
    Summative Assignments
    Students will complete an assignment on each of the Advanced Organic Reactions and Strategies and Tactics of Synthesis course material topics, with each worth 5%. The assignments may comprise a range of formats, including a series of short or long-answer and/or multiple-choice questions or oral presentations.

    Workshop Assignment
    Students undertake the spectroscopy workshop during the first three weeks of normal lab sessions. They are then given a spectroscopy assignment which is worth 10% of the assessment, in which the students answer short-answer questions involving interpretation spectra (UV, IR, MS, 1-D and 2-D 1H and 13C NMR) of unknown samples in order to determine their structure.

    Practical Reports
    Each experiment will be assessed on laboratory results (yield, appearance of product, melting point, graphs, quality of data etc.) as well as the laboratory notebooks and report. Students will complete a set of 5-6 experiments and submit an assessable report on completion of each experiment, which will take various forms from minor written report to extended major report. Students will be provided with sample reports or rubrics with guidelines on report structure and approximate length.  

    Examination
    The final 3-hour examination will examine all components of the course. It may consist of any combination of multiple choice, short-answer and/or long-answer questions.
    Submission
    Submission of Assigned Work
    Coversheets must be completed and attached to all submitted work. Coversheets can be obtained from the School Office (room G33 Physics) or from MyUNI. Work should be submitted via the assignment drop box at the School Office or via MyUni as instructed.

    Extensions for Assessment Tasks
    Extensions of deadlines for assessment tasks may be allowed for reasonable causes. Such situations would include compassionate and medical grounds of the severity that would justify the awarding of a supplementary examination. Evidence for the grounds must be provided when an extension is requested. Students are required to apply for an extension to the Course Coordinator before the assessment task is due. Extensions will not be provided on the grounds of poor prioritising of time. The assessment extension application form can be obtained from: https://sciences.adelaide.edu.au/study/student-support/forms-and-policies#academic-forms

    Late Submission of Assessments
    If an extension is not applied for, or not granted then a penalty for late submission will apply. A penalty of 10% of the value of the assignment for each calendar day that is late (i.e. weekends count as 2 days), up to a maximum of 50% of the available marks will be applied. This means that an assignment that is 5 days or more late without an approved extension can only receive a maximum of 50% of the mark.
    Course Grading

    Grades for your performance in this course will be awarded in accordance with the following scheme:

    M10 (Coursework Mark Scheme)
    Grade Mark Description
    FNS   Fail No Submission
    F 1-49 Fail
    P 50-64 Pass
    C 65-74 Credit
    D 75-84 Distinction
    HD 85-100 High Distinction
    CN   Continuing
    NFE   No Formal Examination
    RP   Result Pending

    Further details of the grades/results can be obtained from Examinations.

    Grade Descriptors are available which provide a general guide to the standard of work that is expected at each grade level. More information at Assessment for Coursework Programs.

    Final results for this course will be made available through Access Adelaide.

  • Student Feedback

    The University places a high priority on approaches to learning and teaching that enhance the student experience. Feedback is sought from students in a variety of ways including on-going engagement with staff, the use of online discussion boards and the use of Student Experience of Learning and Teaching (SELT) surveys as well as GOS surveys and Program reviews.

    SELTs are an important source of information to inform individual teaching practice, decisions about teaching duties, and course and program curriculum design. They enable the University to assess how effectively its learning environments and teaching practices facilitate student engagement and learning outcomes. Under the current SELT Policy (http://www.adelaide.edu.au/policies/101/) course SELTs are mandated and must be conducted at the conclusion of each term/semester/trimester for every course offering. Feedback on issues raised through course SELT surveys is made available to enrolled students through various resources (e.g. MyUni). In addition aggregated course SELT data is available.

  • Student Support
  • Policies & Guidelines
  • Fraud Awareness

    Students are reminded that in order to maintain the academic integrity of all programs and courses, the university has a zero-tolerance approach to students offering money or significant value goods or services to any staff member who is involved in their teaching or assessment. Students offering lecturers or tutors or professional staff anything more than a small token of appreciation is totally unacceptable, in any circumstances. Staff members are obliged to report all such incidents to their supervisor/manager, who will refer them for action under the university's student’s disciplinary procedures.

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